Tony Stewart

Tony Stewart got his first competitive go kart in Westport, Indiana in 1979.[4] In 1980, he won his first championship.[4] He grew up racing go karts and was successful very early, winning a World Karting Association championship in 1987. He moved up to the United Midget Racing Association (UMRA) where he raced TQ (three quarter) midgets until 1991, when he again moved up this time to the United States Auto Club (USAC) series with help from one of his karting sponsors and friend Mark Dismore. Stewart was the USAC Rookie of the Year in 1991, USAC National Midget Series Champion in 1994 and 1995, and USAC Silver Crown Series champion in 1995.

Stewart's 1999 Indianapolis 500 car

In 1995, Stewart became the first driver to win USAC's version of the Triple Crown, earning championships in all three of USAC's major divisions, National Midget, Sprint, and Silver Crown. His winning the Hut Hundred and 4-Crown Nationals were the highlights of the year.

When he was not racing IndyCars, he raced stock cars. In 1996, Stewart made his NASCAR Busch Series debut, driving for car owner Harry Rainer. In nine races, he had a best finish of 16th place. He had more success in a one-time ride in the Craftsman Truck Series with Mueller Brothers racing, where he finished 10th.

Stewart was poised to improve his Indy Racing League (IRL) standing in 1997 but at times he struggled to finish. He failed to finish the first three races of a ten race schedule, but recovered to come in second at Phoenix. At that year's Indy 500, Stewart's car was good enough to enable him to win his first IRL race, leading 64 laps. However, he trailed off near the end of the race and settled for 5th place. He finally got his first career win at Pikes Peak, where he led all but seven laps of a 200 lap race. He became the leading contender for the series' championship after a bad slump knocked points leader Davey Hamilton out of first place. Despite an average end to his season, finishing 7th, 14th, and 11th, and five DNFs, Stewart did just enough to beat Hamilton for the IRL title. He also raced in a few midget events, finishing thirteenth and eleventh in the 1997 and 1998 USAC national points, and winning the Copper Classic both years. Between his time in USAC and the IRL, Stewart earned the nickname of "Smoke", first for slipping the right rear tire during dirt races and then for blowing his engine often during his 1997 championship run.[5]

As he had done the previous year, he raced a handful of Busch Series races in 1998. This time, he was racing for Joe Gibbs, NFL Hall of Fame head coach of the Washington Redskins, who was having major success with Bobby Labonte in the Winston Cup Series. When Stewart was able to finish races, he finished in the top 10, and had a 3rd-place finish at Charlotte. Stewart so impressed Gibbs that he was signed to drive the majority of the Busch schedule in 1998 to go along with a full-time IRL schedule. The double duty did not affect his performance in either series. In the IRL, he won twice and finished 3rd in the championship. His season was a disappointment as he finished last in the Indy 500 because of an engine failure.

On the Busch side, he finished in the top-five five times in 22 starts. He came close to winning his first Busch Series race at Rockingham, but was beaten on a last lap pass by Matt Kenseth. Stewart finished a solid 2nd place in 2 (of 31) starts, ahead of six drivers with more starts, and had an average finish that was comparable to some of the series' top 10 finishers. Gibbs had enough confidence in Stewart that he was moved up to a Cup ride for the 1999 season. With that move, Stewart ended his three-year career as a full-time IRL driver.

After transitioning to the Cup level, Stewart continued racing in the Busch Series on a part-time basis. On August 16, 2005, Stewart was fined $5,000 and placed on probation until December 31 for hitting Brian Vickers after the completion of the Busch Series Zippo 200 at Watkins Glen. He was driving a Busch car owned by Kevin Harvick Incorporated at the time.

In 2013, Stewart renewed his RCR deal to drive the No. 33 Oreos/Ritz Chevrolet. He won the opening Nationwide Series event at Daytona, overtaking Regan Smith on the last lap, but his win was overshadowed by worry because Smith had been turned and in the resulting crash, Kyle Larson had flown into the catchfence, completely slicing off the front part of his car and injuring 28 spectators in the grandstands (2 critically). The next day in the Daytona 500, Stewart's day ended on lap 35, when he was caught up an early crash with Kevin Harvick and Kasey Kahne; this would allow him finish 41st. He rebounded slightly with an 8th-place finish at Phoenix and an 11th-place finish in Las Vegas. At Bristol, Stewart blew his tire on lap 3 and cut a brake line; he came back out over 20 laps down, unable to contend for victory.

In 2020, Stewart planned to make his return to the now-Xfinity Series for the Pennzoil 150 on the Indianapolis Motor Speedway's road course, but plans were called off due to the COVID-19 pandemic.[6][7]

After competing part-time during the 1996 NASCAR Busch Series season with the team, Stewart had planned to move up to the Winston Cup Series in 1997 driving for Ranier-Walsh Racing;[8] however the deal fell through when Stewart decided he was not ready for the move.[9]

Stewart started his Sprint Cup career in 1999 with a bang, as he qualified his No. 20 The Home Depot-sponsored Pontiac on the outside pole for the Daytona 500. He showed courage in one of the Gatorade Twin 125s, when he was involved in a battle with Dale Earnhardt for the lead in the last laps. Though Earnhardt came out on top, Stewart had nonetheless impressed quite a few people with his performance. In the 500, Stewart ran near the front until problems with the car relegated him to a 28th-place finish.

Stewart spent most of his rookie season wowing people, as his car was often in the Top 5. He won a pair of pole positions at short tracks, and set a series record for wins by a rookie with three—Richmond, Phoenix, and Homestead—surpassing Davey Allison's record set in 1987[10] (Stewart's record would hold until 2002, when Jimmie Johnson tied the feat by winning three times; although Carl Edwards won four times in 2005, his first full Cup season, he was not regarded as a rookie by NASCAR standards because he had run more than ten Nextel Cup races in 2004). He finished his first Cup season with 3 wins, 12 top fives, 21 top tens, 2 poles, only 1 DNF, 1,226 laps led, a 10.26 average finish, and a 4th-place finish in the point standings, making it the highest points finish by a rookie in the modern era (which held until 2006 when his future teammate Denny Hamlin finished 3rd) and only bested by James Hylton, who finished 2nd as a first-timer in 1966.[10] Not surprisingly, he ran away with the Winston Cup Rookie of the Year award.

Stewart also attempted to race 1,100 miles (1,800 km) on Memorial Day weekend, as he competed in both the Indy 500 during the day and the Coca-Cola 600 in Charlotte, N.C., at night. He finished in the Top 10 at both races: 9th in the 1999 Indianapolis 500 and 4th at Charlotte. However, he only completed 1,090 miles (1,750 km) of the scheduled 1,100, as he finished 4 laps down at Indianapolis.

Stewart celebrates his 2000 NAPA Autocare 500 win

Stewart showed no signs of a sophomore slump in the 2000 NASCAR Winston Cup Series, winning a series-high[11] six races (Martinsville, New Hampshire, Michigan, Homestead, and both Dover races). However, he fell to 6th place in the standings because of a handful of DNFs and an increase in the number of competitive drivers, among them his teammate Labonte, who won the Cup championship. Stewart also began to get some bad press for his on-track incidents. The best known of these came at Watkins Glen, when he and Jeff Gordon tangled and crashed. Stewart made his displeasure toward Gordon known in an obscenity-laden tirade. Stewart won the Turkey Night Grand Prix midget car event at Irwindale, California, which he called, “one of his greatest wins ever."[5]

Stewart got off to a scary start for the 2001 season: during the Daytona 500, he was involved in an 18-car crash on lap 173. The crash began on the back straightaway and also collected Bobby Labonte and his brother Terry, Rusty Wallace, Steve Park, Jason Leffler, Jerry Nadeau, Buckshot Jones, Andy Houston, Ward Burton, Mark Martin, Kenny Wallace, Jeff Gordon, Elliot Sadler, Dale Jarrett, Jeff Burton, John Andretti, and Robby Gordon. Stewart took the worst of it, as his car turned backwards after being hit by Ward Burton, pushed over Robby Gordon, then flipped twice in midair, hooked Bobby Labonte's hood, and came to a stop in the infield. Stewart was transported to Halifax Medical Center after complaints of discomfort in his shoulder. Stewart's crash was greatly overshadowed by Dale Earnhardt's fatal crash on the last lap. Stewart recovered to win three more races at Richmond, Infineon, and Bristol and, as he had done before, he ran near the front most of the season. Statistically, he had a worse season than 2000, but he finished 2nd to Gordon in the final points standings.

For the second time, Stewart ran the "Memorial Day Double", in spite of a 17-minute rain delay at Indianapolis. He finished sixth in the Indianapolis 500 and third in the Coca-Cola 600, running all 1,100 miles (1,800 km) of the two races.[12]

The 2001 season was not without controversy. Jeff Gordon pulled a "bump and run" on Stewart to gain a better finishing position at Bristol and Stewart retaliated in a post-race incident by spinning Gordon out on pit road. Stewart was fined and placed on NASCAR probation. He got into much bigger trouble in the Pepsi 400 at Daytona, where he confronted a Winston Cup official after ignoring a black flag, which he had received for an illegal pass on Dave Blaney.[13] In the same race, he had an incident with a Winston-Salem Journal reporter in which he kicked away a tape recorder.[14][15] He confronted that same official during the Talladega race after he refused to wear a mandated head-and-neck restraint. Stewart was not allowed to practice until he wore one, and only managed to do so after his crew chief Greg Zipadelli intervened. Stewart's fines and periods of probation resulting from these incidents have earned him a reputation of having a hot-temper, and he became known as NASCAR's "bad boy".

Stewart started the 2002 season even more inauspiciously than last year's, as the Daytona 500 lasted just two laps for him due to a blown engine. He went on to win twice early in the season at Atlanta and Richmond, but he was only seventh in the points standings at the season's halfway point. At Darlington, Stewart was involved in a multi-car wreck in which Jimmy Spencer's car t-boned Stewart's car. While Stewart was sent to the hospital following the crash, he was able the start the next race at Bristol. Due to the injuries sustained at Darlington, he was relieved during the race by Todd Bodine. The second half of his season was plagued by an altercation with a photographer after the Brickyard 400. He was fined $50,000 by NASCAR and penalized with a 25-point deduction. However, despite the controversy, he went on to win the very next week at Watkins Glen. Strangely enough, this race also ended in controversy, when it was revealed that he had jumped the restart and, despite the infraction, officials upheld Stewart's win. Stewart went on a hot streak in the final races, consistently finishing in the Top 5. At the end of the season, Stewart held off a charging Mark Martin to win his first Winston Cup championship. This was Stewart's last season driving in a Pontiac.

As the defending champion, Stewart managed to have a relatively incident-free 2003 season. Joe Gibbs Racing changed manufacturers, so he and Labonte were now driving Chevrolets instead of Pontiacs. Stewart had his worst Cup season at this point up until 2006, but it was still good enough for seventh in the points standings. He only won two races that season at Pocono and Charlotte but he led more laps than he did last year and was highly competitive in the final races of the season.

In January 2004, Stewart teamed with Andy Wallace and Dale Earnhardt Jr. in a Boss Motorsports Chevrolet to take fourth in the 24 Hours of Daytona sports car endurance race. The result does not show the trio's performance, however. They had dominated the race until the last two hours, when the suspension cracked. With 15 minutes left in the race and Stewart driving, one of the rear wheels came off, finally ending their run. In addition to placing fourth overall, the trio placed third in the Daytona Prototype class.

Stewart started off on a higher note in the 2004 season as he finished second in the Gatorade 125. In the Daytona 500, he and Dale Earnhardt Jr. both dominated the race, leading 156 laps overall (98 for Stewart). Stewart was in contention to win it, only to lose the lead to Earnhardt Jr. with 20 laps to go. That would be Stewart's best finish in the Daytona 500.

At Infineon, Stewart was involved in an altercation with rookie driver Brian Vickers. On lap 88 of 110, Stewart got spun out by Vickers as retaliation for an earlier collision in the race. Stewart replied by confronting Vickers after the race and throwing a punch through Vickers' window. Stewart was fined $50,000, stripped of 25 driver & owner points and put on probation for the rest of 2004.

The season was highlighted with Stewart's first win coming at Chicagoland. This win was not without controversy as on a mid-race restart, he turned Kasey Kahne into the wall, which eventually led to an altercation between his and Kahne's pit crews. Stewart felt very sick during the race at Watkins Glen International and nearly withdrew from it due to food poisoning, stomach cramps, a headache, and a sinus infection. He ultimately relented and ran the race, dominating and holding off Canadian road ringer Ron Fellows for the win. He qualified fourth for the first ever Chase for the NASCAR NEXTEL Cup. However, an incident at the first race of The Chase at Loudon ended his hopes of a second Cup championship. Stewart got collected in a multi-car crash, which started when Robby Gordon repaid Greg Biffle some retaliation, and Stewart t-boned Biffle. Stewart had to make repairs and lost three laps. He finished two laps down, causing him to lose his shot at his second championship. Gordon did not get off the hook however and was penalized with a $15,000 fine and a 50-point deduction for his actions.

After losing his bid for the championship title, Stewart finished sixth in the Nextel Cup point standings.

In November 2004, Stewart became the owner of one of the most legendary short tracks in America, Eldora Speedway. Located in New Weston, Ohio, Eldora is a half-mile dirt track known to many as "Auto Racing's Showcase Since 1954." Stewart began racing there in 1991 and continues racing in special events alongside other Sprint Cup drivers and dirt track legends.

Stewart on two wheels before going on to win the 2005 Dodge/Save Mart 350, at Infineon Raceway

2005 was one of Stewart's most successful years in the Nextel Cup Series as he won his second Cup title. He won five races at Infineon, Daytona, New Hampshire, Watkins Glen (which gave him a sweep of the road course races for the year and a record 3 straight road course wins) and Indianapolis, his hometown track (in a race that Stewart said he would give up his championship to win, and took with it the No. 1 seed heading into NASCAR's Chase for the Nextel Cup 10-race playoff).

Stewart's 2005 Allstate 400 at the Brickyard winning car on display at the Indianapolis Motor Speedway museum.

Following his win in the Pepsi 400, Stewart began climbing the fence separating the fans from the race track after each victory, borrowing IndyCar Series driver Hélio Castroneves' trademark move.[16] After winning the 2009 All-Star race, Stewart was quoted as saying "I'm too damn fat to be climbing fences," and recently purchased $17,000 worth of exercise equipment to remedy the problem. It also led to sponsor The Home Depot cashing in on Stewart's success with some promotions reminiscent of Stewart's Eldora Speedway drivers. After his second full climb of the fence in Loudon, N.H., they ran a discount on ladders and fencing at the stores with a campaign named, "Hey Tony, we've got ladders", where anyone who presented the advertisement in national newspapers in their stores earned the discount. After his victory in Indianapolis, The Home Depot presented fans who presented the advertisement of his Allstate 400 win with a discount on purchasing bricks. He mentioned in a press release from his sponsor, "I plan to keep winning races and helping to drive down the cost of home improvement for The Home Depot customers."

On November 20, 2005, Stewart won his second Cup Championship, joining Jeff Gordon as the only active, full-time drivers at the time to have won multiple championships. Jimmie Johnson afterward did so from 2006 to 2010. In victory circle, Stewart had said that he loved winning his 2005 championship better than his 2002 one because his 2005 season was more well-behaved than 2002. At an age of 34, this made Stewart one of the youngest drivers to win multiple championships (with Johnson joining this category as he won his five straight titles while in his early 30s) and to date, he is still the only driver to have won championships under both the Chase and non-Chase formats. During the 2005 season, Stewart won a total of $13,578,168, including $6,173,633 for winning the championship, the largest season total in NASCAR history.

Stewart's 2006 season had up and down notes. He had competitive cars and scored early wins at Daytona and Martinsville. However he also had strings of bad luck. He also suffered a shoulder injury due to two heavy crashes in both the Busch and Cup races at Charlotte during the Memorial Day Weekend races (Stewart's Busch car hit the Turn 4 wall so hard it even knocked the rear end off the car). During the Dover race, he was substituted by Ricky Rudd and, in later weeks, had to drive in pain.

Additionally he has once again been involved in several on track controversies.

Following a rough Bud Shootout on February 12, 2006 Stewart expressed concern to the media about the possibility of aggressive driving resulting in the serious injury or death of a driver. It came during a week in which the racing world remembered the fifth anniversary of Dale Earnhardt's death. Just a few days later, during the Daytona 500, Stewart was involved in a number of incidents with Jeff Gordon, Kyle Busch, and Matt Kenseth, whom he chased halfway across the track to run into the grass. "He has no room to complain," Stewart said of his brush with Kenseth. "He started it, and I finished it".

On May 20, 2006, during NASCAR's All Star Race, Stewart and Kenseth wrecked again. Each driver claimed it was the other one's fault with Stewart saying, "if (Kenseth) thinks it's my fault and I (caused the wreck) he's screwed up in his head." Following the wreck, several media outlets proclaimed the new Stewart-Kenseth rivalry as must-see TV.[17] The so-called rivalry was short-lived as Kenseth and Stewart participated as friends in a joint promotional tour for DeWalt and The Home Depot;[18] Kenseth also appeared in September at Stewart's Eldora Speedway in the NEXTEL PRELUDE with NASCAR drivers, as well as the ARCA Truck Series event there.

On July 1, 2006, Stewart dominated the Pepsi 400 but after a pit stop seemed like an unlikely contender for the win. However, Stewart amazed the audience when in the final 10 laps he drove from 14th up to second place, and passed Boris Said to take the lead and win. After the race Stewart said he no longer wanted to climb the catch-fencing at Daytona because of the fans crowding him but he later changed his mind on that thought.

On July 23, 2006, Stewart once again was at the center of a media storm. On lap 31 of the Pennsylvania 500, Stewart was accidentally squeezed against the wall by Clint Bowyer. Stewart responded by waving his hand in anger, then purposely hitting Bowyer's car. This contact sent Bowyer spinning down the front stretch where he collided with Carl Edwards. Stewart was promptly held one lap by NASCAR for rough driving. He did however pass leader Ryan Newman to get back on the lead lap and eventually rallied to finish 7th and get back in the top 10 in the point standings. After initially refusing to take responsibility for the incident he apologized the next day.[19]

Stewart missed the cut to qualify for the 2006 Chase for the Nextel Cup by 16 points,[20] becoming the first defending champion to miss the Chase the following year.[21] He finished poorly at Richmond after wrecking his primary car in practice, and was displaced in the top ten by Kasey Kahne. As a result, he finished the 2006 season 11th in points, his worst thus far in his career, as he had completed each of his seven previous seasons in the top ten in points. Commenting on not being in the 2006 Chase, he says: "It lets us have the ability to take chances and try things ... that we've been wanting to try but just haven't had the luxury to do it. If we were in the Chase we wouldn't have that ability".[22] Stewart won three races in the 2006 Chase (Kansas, Atlanta, and Texas).

The season was not totally unkind to Stewart, however. He was a participant in the 30th season of IROC and won 2 of the 4 races (Texas, and the Daytona road course) on his way to capturing the series championship. He won a million dollars for the effort, but made an offer to return his prize money if IROC would hold one of its events at his Eldora Speedway. This offer was not entertained as IROC folded in 2007. In addition, Stewart's three wins in the Chase races gave him five total for the season, tying him with Jimmie Johnson and Kevin Harvick for second most in Nextel Cup behind Kasey Kahne's six.

Stewart races by at Texas Motor Speedway in 2007.

Stewart started the 2007 season by winning his second Chili Bowl Nationals midget car feature. Stewart started off the Daytona Speedweeks with a win in the 2007 Budweiser Shootout. It was his third win in the race.[23] He also won his qualifying race for the Daytona 500.

On lap 152 of the Daytona 500, the rear of Stewart's car slid up the track and, when he tried to cut down the track, he smacked the front of Kurt Busch's car knocking both of them out of the race. Stewart and the Busch brothers (Kurt and Kyle) were the three leaders for the majority of the race.

On March 22, 2007, it was announced that Stewart would be on the cover of the official NASCAR video game NASCAR 08, published by Electronic Arts. This would be the third time this honor was given to Stewart (2001, 2004, 2008).

In his first Car of Tomorrow race with the Impala SS, Stewart was dominant at Bristol, leading 257 of 504 laps (green-white-checker finish), before he experienced a fuel pump problem. In his third Car of Tomorrow race at Phoenix, Stewart lead a race high 132 laps, but a late race caution moved Stewart to 2nd, where he finished behind Jeff Gordon. In the following week, Stewart implied the cautions were "bogus" and that NASCAR is "rigged like professional wrestling".[24]

On June 4, 2007, Stewart and Kurt Busch had another altercation on pit road in the Autism Speaks 400 at Dover. Kurt Busch passed Stewart on the inside and then slid up, which caused contact, sending him into the wall, knocking out Busch, but with Stewart staying in the race. Initially it was thought that Stewart intentionally crashed Busch since they were bitter rivals over the year and had had contact early in the race. Under the caution, Stewart was on pit road and his crew was surveying the massive damage he received from the crash; when an enraged Busch pulled alongside and gave Stewart a profane gesture to express his feelings over the incident. One of Stewart's pitcrew members jumped out of the way of Busch's car to avoid being hit, while Busch was disqualified. Stewart was put on temporary probation for his part in the feud but was cleared from any further penalties.

At the All-Star Race at Charlotte, he finished 5th behind Kevin Harvick, Jimmie Johnson, Mark Martin, and Jeff Burton. At the Coca-Cola 600, Stewart finished sixth, after having to come in to pit for fuel.

On July 15, 2007, Stewart led a race high 108 laps and recorded his 30th career NEXTEL Cup win at the USG Sheetrock 400 at Joliet.

On July 29, 2007, after leading a race high 65 of 160 laps, Stewart won the Brickyard 400 again, just 45 minutes from where he grew up. This was his second win in the race at his favorite track. It was not without controversy though; Stewart made the winning pass by accidentally bending the rear of Kevin Harvick's car, causing Harvick to fall back quickly to seventh place by the time the checkers waved. Stewart apologized for the contact in victory lane and during the victory lane interview, Stewart was penalized 25 points and fined $25,000 for violating NASCAR's policy on the use of obscene language during interviews during the race. This was similar to 2004, when Dale Earnhardt Jr. used an obscenity in a post-race interview at Talladega and was knocked out of the points lead as a result of the penalty.

On August 12, 2007, he won the Centurion Boats at the Glen at Watkins Glen after Jeff Gordon spun his car around after wheel hopping in turn 1 with two laps to go. Carl Edwards briefly challenged Stewart on the final lap, but spun out into a pullover site sealing Stewart's win.[25]

Stewart's Toyota Camry.

Stewart began the 2008 season with a 6th-place start in the Daytona 500. During this race, he was only able to come up with a 3rd-place finish after being passed by Ryan Newman and Kurt Busch on the last lap. The finish of this race was somewhat like a repeat of the previous year's Daytona 500, in which Stewart's close friend Kevin Harvick passed Mark Martin to win it.

On lap 109 of the UAW-Dodge 400, Stewart's car cut a tire and slammed hard into the turn 3 retaining wall. Although he climbed out under his own power, Stewart was transported by ambulance to the infield care center. Stewart had complained about a sore foot from a wreck that occurred the day before the Nationwide Series race at Las Vegas. Stewart was later announced that he was okay and ripped on Goodyear for not bringing any quality tires.

With 3 laps to go in the 2008 Coca-Cola 600, Stewart cut a tire and saved it from contact with the wall. However, Stewart had to give up the lead to future race winner Kasey Kahne in order to make pit stops.

In the Best Buy 400, Stewart was involved in another crash with Elliott Sadler, in which Sadler got turned by David Gilliland and car collected Stewart and 11 other cars; those included Dale Earnhardt Jr. and Denny Hamlin. Stewart, who was frustrated over his misfortune, sarcastically said, "I take 100 percent responsibility – it's my fault for being anywhere close to Elliott. If I'm within half a lap of him, I expect that to happen. It's my fault – I'm the one that hit him. When I hit him, it caused all the guys behind us to wreck, so it's my fault."

In July 2008, Stewart made a deal with car owner Gene Haas into a co-owning partnership in a racing organization called Stewart-Haas Racing for 2009 when he left Joe Gibbs Racing. Ryan Newman came to the meeting to make his deal with SHR officially signed earlier in the year.

On July 5, 2008, during the Coke Zero 400 at Daytona, Stewart started feeling ill and turned his car over to former Joe Gibbs Racing teammate J. J. Yeley, who took the car to a 20th-place finish after getting involved in two wrecks in the last 5 laps.[26] Stewart earned his first and only win of the season in the AMP Energy 500 at Talladega on October 5, 2008 driving for Subway as his sponsor, making it his last win with Joe Gibbs Racing. On the final lap, Stewart was passed by Regan Smith (the rookie of Dale Earnhardt, Inc.) who beat Stewart to the line. NASCAR declared that Smith had made an illegal pass under the yellow line, and awarded the victory to Stewart.[27]

After the Ford 400, Stewart attended a tearful farewell meeting with Joe Gibbs Racing and gave his car and team to rookie Joey Logano, who replaced him for JGR.

Stewart pits his No.14 Impala in the 2009 Coca-Cola 600 at Charlotte Motor Speedway.

On July 8, 2008, it was reported that Stewart was released from the last year of his contract with Joe Gibbs Racing, primarily because JGR had switched from Chevrolet to Toyota, and Stewart was vocal about his loyalty to Chevrolet (which sponsors his USAC Midget, Sprint Car, and Silver Crown teams). Stewart announced he would move to Haas CNC Racing to drive a Haas Chevrolet, with sponsorships from Office Depot (relocating from the No. 99 Roush Fenway team) and Old Spice. Stewart took half ownership of the team which was renamed Stewart-Haas Racing, and Stewart became the highest paid NASCAR driver. Stewart's car at Haas has the number 14 as homage to his hero A. J. Foyt.[28] To date, he is the most successful driver for Joe Gibbs Racing with 33 wins and 2 championships (2002 and 2005).

On August 15, 2008, fellow Indiana native Ryan Newman signed a multi-year contract to drive the second car for Stewart-Haas Racing, originally to be designated No. 4 but changed to his USAC No. 39, with sponsorship from the U.S. Army (relocating from Earnhardt Ganassi Racing).

As the most recent series champion not among the Top 35 in owners' points, Stewart was first in line for past champions' provisionals for the first five races of 2009. He completed those races without needing to use the provisional, ending up well inside the Top 10 in points. Stewart won his first race as a driver/owner in the non-championship NASCAR Sprint All-Star Race XXV, winning more than $1,000,000, his first win in the event in 10 attempts. He followed that victory with his first points race win as a driver/owner at Pocono in the Pocono 500 on June 7, 2009, the first owner-driver in the Cup series to win a race since Ricky Rudd in 1998.[29] Stewart also won the Coke Zero 400 at Daytona after a controversial finish when he wrecked Kyle Busch to do so. In a similar fashion to the spring race at Talladega that year, Busch passed Stewart on the final lap but in the final turn Stewart went underneath Busch who tried to block but with 100 feet left from the checkers the two made contact resulting in Stewart sending Busch into the wall, and Busch wrecked across the line in the final lead position while Kasey Kahne submarined under his car.

Stewart's season overall was his best showing since his rookie year, with another win coming at Watkins Glen International. Stewart qualified for the 2009 Chase for the Sprint Cup as he finished the first 26 races as points leader. He fell to second in points following reseeding when Mark Martin, who won more races than Stewart, moved ahead of him. On October 5, 2009, Stewart won the Price Chopper 400 and moved to fourth in the standings, ending the season in sixth place.

Stewart after winning the 2010 Pepsi Max 400

On April 16, 2010, Stewart won his first Sprint Cup pole position in five years at Texas Motor Speedway, with a lap speed of 191.327 mph. The race was the 400th in the Sprint Cup for Stewart, and was his first starting from the pole since October 2005 at Martinsville Speedway.[30]

On May 9, 2010, it was reported that Stewart would lose Old Spice as a sponsor after 11 years with them.[31]

Stewart won two races in 2010: the Emory Healthcare 500 at Atlanta Motor Speedway on September 5, 2010 and the Pepsi Max 400 at Auto Club Speedway on October 10, 2010.

In September at Loudon, Stewart lead part of the final stages trying to hold off Clint Bowyer for RCR who dominated the race; when the white flag waved the fans saw that Stewart was out of gas; Bowyer passed him and won both the white flag and the checkers. Stewart finished 24th, and waved to Bowyer to congratulate him as he slowly crossed the line to finish. After the race Stewart said when interviewed "My feelings are not happy that's for sure but we had a strong race; I thank Office Depot, Coca-Cola, and my sponsors... congratulations to Clint Bowyer and the helping hands, they deserved that one. I think I ran myself out of fuel; my team apologized and said "sorry for running you out of fuel", I think I ran myself out of fuel."

On October 12, 2010, Mobil 1 announced a sponsorship deal with Stewart-Haas Racing to sponsor Stewart's car, starting in 2011. It would be the primary sponsor for 11 races, while Office Depot would be the primary sponsor for the rest of the season. Mobil 1 would also sponsor Stewart in the Budweiser Shootout and the All-Star Race.

Stewart during the 2011 Toyota/Save Mart 350

In 2011, Stewart returned in the No. 14 Office Depot-sponsored Chevrolet. Following a crash intentionally caused by Stewart on Brian Vickers at Infineon Raceway in June 2011, Vickers intentionally wrecked Stewart as payback. In an interview when asked about the crashes, Stewart said, "It was payback, but, you know, I dumped him first, and I dumped him because he was blocking..."[32] Stewart and his teammate, Newman, started the Lenox Industrial Tools 301 first and second, and they finished it where they started as Newman won that race. By the Heluva Good! Sour Cream Dips 400, Stewart said in a post-race interview that his team was running so poorly that he was "wasting one of those top 12 spots." Entering the Chase for the NASCAR Sprint Cup portion of the schedule winless, Stewart won the opening race of the Chase at the Chicagoland Speedway and jumped up seven spots in the points, securing second place and extending his streak of consecutive years with a win to 13. Stewart made it two for two in the Chase after Clint Bowyer ran out of fuel in the closing laps of the Sylvania 300 at the New Hampshire Motor Speedway. Stewart took the win and the points lead after New Hampshire. At Talladega, Stewart struggled to lead a lap, and eventually did so; with assistance from Ryan Newman, Paul Menard, and Joey Logano, he led an additional 29 laps and captured the two-point bonus for leading the most laps. On October 30, 2011, at Martinsville Speedway, Stewart won the Tums Fast Relief 500, leading three times for 14 laps and moving into championship contention in second place in the points standings.

The next week, Stewart led 173 laps en route to winning the AAA Texas 500 at Texas Motor Speedway, bringing him to within three points of championship points leader Carl Edwards with two races to go in the 2011 season. On November 20, 2011, Stewart won the NASCAR Sprint Cup Series championship by winning the final race at Homestead-Miami Speedway while Edwards finished second.[33] Stewart and Edwards were tied on total points, but Stewart claimed the tiebreaker by having five race wins, all during the Chase, to Edwards's one win.[34] In the process, Stewart became the first driver/owner to win the championship since Alan Kulwicki in 1992.

Stewart during the 2012 Kobalt Tools 400

Before the season Stewart welcomed new drivers retired Indycar driver Danica Patrick and driver David Reutimann to drive partly for Stewart-Haas Racing as part of a partnership with Tommy Baldwin Racing who provided parts of the cars.

On February 11, 2012, Stewart led the final stages of the Budweiser Shootout by passing Marcos Ambrose on the final lap, but was passed in a desperate charge to the finish line by Kyle Busch who beat him to the line in what was said the closest finish in Budweiser Shootout history (It would have been 2011 with Kurt Busch and Denny Hamlin but Hamlin was black-flagged for being below the yellow line). Stewart won the 1st duel of the Gatorade Duels at Daytona, when his new driver Danica Patrick hit the wall hard on the backstretch on the final lap, which brought out the caution. Stewart started 3rd in the Daytona 500 and ran well throughout the race, but was caught up in a late race crash on lap 196 Ricky Stenhouse Jr. On March 11, Stewart won the Kobalt Tools 400 at Las Vegas Motor Speedway beating Jimmie Johnson. It was his 45th career win, and brought his streak of consecutive Cup seasons with a win to 14.

On March 25, 2012, Stewart won the rain-shortened Auto Club 400 at Auto Club Speedway. On June 3, 2012, Stewart was caught in a 13 car crash on the back leg at Dover and finished the race in 25th place.

Tony Stewart led 18 laps at the 2012 Quicken Loans 400 and finished second behind Dale Earnhardt Jr.. Stewart however caused controversy and got ripped by the fans and medias for saying in a media conference that Earnhardt winning "Is not a national holiday." and taunting the Earnhardt nation for celebrating the 4th anniversary of Earnhardt's last win in 2008.

At Sonoma, Stewart moved quickly from the top 20, to third in the final laps of the Toyota Save Mart 350, and ended up second to Clint Bowyer by passing Kurt Busch on the final turn on the final lap. On July 7, Stewart was able to hold off Matt Kenseth to win his fourth Coke Zero 400 as a wreck ensued behind him. The win was a surprise one, as Stewart had been forced to start 42nd due to his car failing pre-qualifying inspection.

In August at Bristol in the 2012 Irwin Tools Night Race, when battling for the lead on lap 333, Stewart and Matt Kenseth tangled and brought out a caution. This was soon after Ryan Newman was wrecked by Juan Pablo Montoya in an accident which collected Jeff Burton. When a furious Stewart climbed out of his wrecked car he waited for Kenseth to exit pit road. When Kenseth was leaving the pits, in Stewart fashion, he tossed his helmet at Kenseth's hood and then gestured applause at the fans. This was followed shortly thereafter by his student driver Danica Patrick wagging a finger at Regan Smith after he turned her into the inside wall many laps later.

In September at Atlanta, team spokesman Mike Arning announced that Office Depot will not be Stewart's sponsor in 2013.[35]

On October 2, 2012, Bass Pro Shops announced they would be a co-primary sponsor for Stewart in a selected number of races for the 2013 season.[36]

At the Talladega race in the fall, Stewart was leading on the final lap but underestimated the speed of a closing Michael Waltrip. On turn 4, Waltrip got a run, and tapped Stewart from behind, causing Stewart to spin and Waltrip to spin into the pack, causing a Big One that involved 23 cars, the largest crash of the season to date. Stewart flipped over, hitting the roofs of several other cars, including Kasey Kahne, Paul Menard, and Clint Bowyer, before landing upright. On November 9, it was announced that Kevin Harvick would be joining Stewart's team starting in 2014.

Stewart would finish ninth in points, with two top fives and four top tens in the Chase, for a final season total of three wins, 12 top five and 16 top ten finishes overall.

Stewart during the 2013 Coke Zero 400

In early 2013, reports said that Stewart was offered a chance by Roger Penske to race in the 2013 Indianapolis 500 in a Penske car. Stewart declined and said he was not ready to try the big race yet, due to his focus in stock cars.[37]

In the Daytona 500, Stewart's day ended on lap 35, when he was caught up an early crash with Kevin Harvick and Kasey Kahne; this would allow him finish 41st. He rebounded slightly with an 8th-place finish at Phoenix and an 11th-place finish in Las Vegas. At Bristol, Stewart blew his tire on lap 3 and cut a brake line; he came back out over 20 laps down, unable to contend for victory.

At Fontana, Stewart ran well for most of the day, leading laps and running on an alternate pit cycle, and nearly contended for the win. However, due to a late-race incident when Joey Logano blocked him on the last restart, Stewart ended up in 22nd place at the bottom of the lead lap. After the race, Stewart, angered, confronted Logano, who had just wrecked his car after battling with Denny Hamlin hard into the last turn, on pit road in a scuffle involving both teams' crews.[38]

At Richmond, Stewart looked to be in contention for the win as he was 5th on a green-white-checkered finish, but in a fashion similar to his confrontation with Logano at Fontana; after a poor restart he lost a few positions. On the last lap, Kurt Busch tapped his bumper, moving Stewart out of the 2nd groove all the way up to the top of the race track subsequently losing about 5 positions coming home 18th while Busch took a 9th-place finish. Stewart showed his displeasure with Busch after the race had finished, rubbing with him on the race track leading to a shoving match between the two when slowing down after the race ended. Down near the haulers the two turned the attention given to race winner Harvick; to them when they had a verbal confrontation, again Stewart showing Busch his displeasure with his aggressive move. It was the first time since 2008 that the two got together in a feud.

At Talladega, Stewart was caught up in a 15 car wreck on lap 43 and ended up finishing 27th, 5 laps down. His teammates Danica Patrick and Ryan Newman were caught up in a later wreck on lap 182, in which Newman's car got crushed when Kurt Busch flipped over and landed on top of it.

Stewart after winning the 2013 FedEx 400

Stewart's 2013 season start was considered his worst start to a Sprint Cup season yet. As of Richmond, he had only one Top 10 finish, which was at Phoenix. The rest of his finishing positions had been in the upper 10's or lower 20's. After Richmond, Stewart was 22nd in the points standings with 207 points, 136 behind Jimmie Johnson. However, he showed signs of a rebound in the following weeks, scoring a solid 7th-place finish at the Coca-Cola 600 while avoiding several wrecks.

The following week at Dover, Stewart went a lap down early but got back on the lead lap with a beneficiary. In the last 20 laps, after Johnson was penalized for jumping the last restart, Stewart overtook Juan Pablo Montoya and held him off over the last three laps to score his sole Sprint Cup win of 2013. The win propelled him up 4 positions to 16th, into a Wildcard spot. This also gave Stewart a streak of 15 straight seasons with at least one race win. He followed this up with a fourth-place finish at Pocono and a fifth place at Michigan. His momentum was killed briefly by a 28th-place run at Sonoma and a 20th-place finish at Kentucky, but Stewart then rebounded to a second-place finish at the Coke Zero 400.

At New Hampshire, Stewart led 84 laps and was overtaken by Brian Vickers with 14 laps to go. A caution that led to a green-white-checkered finish ultimately ruined Stewart's chances of winning, as he ran out of fuel after the restart while Vickers took the win. Stewart then rebounded with a 4th-place run at Indianapolis and a 9th-place run at Pocono.

The day after the Pocono race, on August 5, 2013, while leading a sprint car race at Southern Iowa Speedway in Oskaloosa, Iowa, Stewart was involved in a multi-car crash when a lapped car spun in front of him. The hit was hard enough that Stewart broke both the tibia and fibula bones in his lower right leg. He was taken by ambulance to a local hospital where surgery was performed on his broken leg.[39][40] A second surgery was performed on August 8, 2013 in which a metal rod was inserted into the tibia.[41] The injuries were bad enough that Stewart's streak of 521 consecutive Sprint Cup starts, dating back to the 1999 Daytona 500, ended. A replacement driver for the August 11 race at Watkins Glen International was not immediately named,[42] though it was eventually announced that road veteran Max Papis would fill in for Watkins Glen.[43] Stewart was eventually released from the hospital on August 11.[44]

Prior to August 11, 2013, speculation arose regarding who would replace Stewart on the oval courses, with speculation that the replacement would either be Regan Smith,[45] who drove two races in Dale Earnhardt Jr.'s car after Earnhardt was sidelined with a concussion in 2012,[46] or Austin Dillon. It was announced after Watkins Glen that Dillon would drive Stewart's car for Michigan.[47] On August 19, 2013, Stewart was ruled out for the remainder of the season. Mark Martin was released from his contract with Michael Waltrip Racing and signed on to drive Stewart's car for the remaining thirteen races of the year, with the exception of Talladega, where Dillon drove the car. Brian Vickers and Elliott Sadler would drive the No. 55 for races Martin was originally intended to drive for MWR in.[48]

Stewart during the 2014 Toyota/Save Mart 350

Before the season it was announced that Stewart had been medically cleared to race. Stewart mentioned during Pre-Season Thunder that his leg would be about 65% healed going into Daytona.[49] Stewart ran the Sprint Unlimited and was collected in a nine-car crash, though he was able to exit his car under his own power and without any pain. Stewart entered the Daytona 500 in his backup car, starting from the rear of the field. After the 6 hour and 22 minute rain delay, the race resumed, but just shy of half way, Stewart's fuel pickup began to fail. His crew repaired the problem in the garage and allowed Stewart to return to the track, finishing the race 27 laps down.

The next week at Phoenix, Stewart ran in the top-ten most of the day. A late string of cautions set up multiple restarts and Stewart opted to come down to pit road to be serviced each time the caution was thrown, subsequently losing track position. On the last and final restart, Stewart had 4 fresh tires and was starting 19th. He gained 3 positions, from 19th to 16th, where he finished. Stewart gained 12 spots in the standings, from 32nd to 20th.[50]

At Las Vegas, Stewart struggled with the handling of his car and finished 33rd, four laps down.

At Bristol, Stewart missed the second round of knockout qualifying and started 37th. However, with a fast racecar, he was able to make his way up the field and finish fourth, his first top-five finish since the previous year's Brickyard 400. Stewart was the highest finishing Chevrolet in the race.

Stewart qualified 10th at Auto Club. After a spin early in the race, Stewart was running 12th at the last caution, coming off of pit road 2nd and lining up 4th for the green-white-checkered finish behind Paul Menard, his own driver Kurt Busch, and Landon Cassill. On the final restart, Stewart and Busch battled for the win, only to be passed up by Kyle Busch and Kyle Larson. Stewart finished third not being passed by Matt Kenseth, his fifth top 5 in a row.

Stewart had a strong run at Pocono. He qualified in the top five and ran in there nearly the whole race, before a speeding penalty on pit road left him with a 13th-place finish. When Stewart was asked about what happened he said "It was a 100% driver error. Last week I cried over a 6th place finish and I just threw this one away. 100% driver error. My fault."

At Michigan, Stewart ran in the top-five. Late in the race Stewart tangled with rookie Kyle Larson when Larson threw a block, leaving Stewart with an 11th-place finish. Stewart replied by bumping Larson under yellow and side-swiping him. The next week Stewart said "He'll learn not to block me. One way or another he'll learn like I did at his age."

After the Kevin Ward Jr. tragedy in mid-August, Stewart skipped Watkins Glen, Michigan and Bristol. He was subbed by Regan Smith and Jeff Burton for those races. Despite having missed three races and thus losing too many points to recover lost points in the final 2 races, NASCAR granted him a waiver allowing him to still be eligible for the Chase if he won in the final two 'regular season' events, which he failed to do, causing him to miss the Chase for the third time in his career.[51]

At the end of the October Charlotte race, Stewart was hit on pit road by Brad Keselowski, who was trying to run into Matt Kenseth, but missed. Stewart retaliated by reversing into him, smashing Keselowski's front in.[52] Stewart was fined $25,000 and placed on probation until November 12, 2014 along with Keselowski who was fined $50,000.[53]

At Martinsville, Stewart almost won. On the final restart, he pulled out in front of Dale Earnhardt Jr. but having older tires, got over-taken by Earnhardt with four laps to go. Stewart finished 4th but stated that after what he went through from August to then, finishing 4th felt like a win to him.

Stewart finished the year with a last-place finish at Homestead-Miami, ending his 15-year winning streak. As a driver, 2014 was Stewart's worst year statistically. The season ended on a positive note for Stewart, as he won the Owner's Championship with Kevin Harvick. In an interview the day before the race, Stewart blamed his subpar year on the new rules package, saying it did not complement his driving style. He also dismissed countless claims that his poor showing had anything to do with his 2013 leg injury.

On February 15, 2014, Stewart returned to sprint car racing in his No. 14 sprint car, the very car that broke his leg in 2013. When asked why he returned, Stewart said he loved racing sprint cars too much to leave. Stewart silenced his critics by dominating and winning a sprint car race at Tri-City Motor Speedway in a huge comeback story. After the race Stewart said:

It was a confidence boost for me. When you haven't won and haven't been necessarily a contender, you start questioning what is it in the equation that you're missing. Is it something that you're doing or not doing as a driver? To be able to win and have two good runs like that in a car that I haven't been in for almost a full year now, that was a huge confidence boost.

Stewart racing at New Hampshire Motor Speedway in 2015

Stewart did not do as well in the 2015 season as hoped, as he failed to score a win for the second year in a row and missed the Chase. He even failed to finish higher than 6th-place for the first time in his career. He showed signs of a comeback after qualifying runs of 4th at Indianapolis, 5th at Pocono, 3rd at Watkins Glen, and 5th at Michigan. Bad calls by crew chief Chad Johnston, the aero package not complementing Stewart's driving style, and a string of bad luck further contributed to his woes.

In August, Stewart lent his private plane to the family of IndyCar driver Justin Wilson so they could fly out to Long Pond, PA, after Wilson was severely injured during a late-race crash; Wilson died several hours later.

On September 27, 2015, Bob Pockrass reported that Stewart announced plans to retire from racing at the conclusion of the 2016 season. Stewart formally made an announcement on September 30, 2015 confirming this and announcing that Clint Bowyer would replace him in the No. 14 in 2017.[54]

On January 31, 2016, Stewart injured his back while riding a dune buggy outside of San Diego[55] with fellow driver Greg Biffle.[56] Four days later, Stewart-Haas Racing announced he had suffered a burst fracture in his lumbar vertebra, which would prevent him from competing in the Daytona 500.[57] Stewart was replaced by Brian Vickers[58] and Ty Dillon.[59] Stewart missed the first eight races of the season. On April 24, 2016, Stewart returned to racing in the Toyota Owners 400 at Richmond,[60] where he finished 19th. Before the Richmond race, NASCAR granted Stewart a waiver from the rule saying that a driver must attempt every race to be eligible for the Chase. If Stewart won a race and finished in the top 30 in the standings by the autumn Richmond race, he would qualify for the 2016 Chase for the Sprint Cup.

For the running of the GEICO 500 at Talladega, Stewart would struggle at the beginning of the race but he would switch with Ty Dillon after the first caution and Dillon would drive the rest of the race; the doctor advised Stewart not to drive the whole race to avoid further injury. The No. 14 car would get the free pass after the first caution. Dillon would finish 7th, but Stewart would get the credit since he started the race and would get his first top 10 of the year. He finished 12th at Kansas the following week. At Michigan for the running of the FireKeepers Casino 400, Stewart would have his best race of the year so far, he would qualify a strong 3rd and run great all race long and would finish 7th.

Stewart after winning the 2016 Toyota/Save Mart 350

The very next week at Sonoma, Stewart took advantage of a late caution and was able to lead the last 20 laps, winning for the first time in three years after making a last lap pass on Denny Hamlin, who wheel-hopped in the final turn and hit the wall after Stewart slipped into the inside. The win was very popular amongst the garages and the win vaulted Stewart from 34th to 31st in the standings, just 9 points out of the top 30. Then the next race at Daytona, Stewart finished 26th due to a late wreck, but moved up to 30th in the points and currently is part of the Chase for the first time since 2012. He did much better at Kentucky, finishing a solid 5th and further propelling him to 20th in owner's points. The next week at New Hampshire he would continue his streak of strong races and get a 2nd-place finish, followed by two 5th-place finishes at Pocono and Watkins Glen.

At Richmond, Stewart was involved in controversy with 28 laps to go in the race. Stewart, while racing former teammate Ryan Newman for 10th place, wrecked Newman in turn 3, causing a five-car pileup and ending Newman's chase chances. In an interview minutes after the crash, Newman was outspoken about his displeasure against Stewart and said "I guess he thought he was in a sprint car again and didn't know how to control his anger. It's disappointing that you have somebody who should be retired the way he drives. It's just ridiculous." Stewart's bid for a fourth title ended after poor finishes caused him to be eliminated from the first round of the Chase. After having his final top-ten at the 2016 Bank of America 500, Tony Stewart wrapped up his 18-year career in Cup competition with a 22nd-place finish at the 2016 Ford EcoBoost 400 where he was 2 laps down.

Prior to the 23rd running of the Brickyard 400, Stewart was inducted into the USAC Hall of Fame in recognition of his sterling United States Auto Club (USAC) career. He was the 1994 USAC National Midget champion; in 1995, Stewart became the first driver ever to claim all three of United States Auto Club National championships in a single season and is one of only six USAC “Triple Crown Champions.” To date, Stewart racing has also won seven USAC Silver Crown Series titles.[61]

Stewart has raced in a few sports car races, including the Rolex 24 at Daytona.

• 2002: Competed in the Rolex 24 on 2/2-2/3 for the Crawford factory team with co-drivers Jan Lammers and Johnny Mowlem.
• 2004: Competed for the second time in the Rolex 24 on 1/31-2/1 for Howard-Boss Motorsports with co-drivers Dale Earnhardt Jr., and Andy Wallace. Team led 355 of 526 laps and had a commanding five-lap advantage before mechanical problems less than 20 minutes short of the finish ended their shot at victory and placed them a disappointing fourth.
• 2005: Competed for the third time in the Rolex 24 on 2/5-2/6 for Howard-Boss Motorsports with co-drivers Jan Lammars and Andy Wallace. Team was leading with less than two hours remaining when a broken gearbox dropped them off the lead lap. Crew was able to make repairs so that the trio could rejoin the race, whereupon they finished third. It was Stewart's first podium finish in the Rolex 24 Hours At Daytona.
• 2006: Competed for the fourth time in the Rolex 24 on 1/28-1/29 for Howard-Boss Motorsports with co-drivers Butch Leitzinger and Andy Wallace. Team finished 30th after suffering mechanical problems throughout the event.
• 2007: Competed for the fifth time in the Rolex 24 on 1/27-1/28 for Howard-Boss Motorsports with co-drivers Butch Leitzinger and Andy Wallace. Team finished 48th after mechanical trouble hampered the trio throughout the event.

United States Secretary of Defense and grand marshal Donald Rumsfeld (left) and Stewart share a laugh before the 2005 Pepsi 400

Stewart has enjoyed a highly successful career in USAC; he has 27 USAC National Midget wins to his credit, as well as 10 wins in the Sprint cars and three in the Silver Crown series. He is also a member of the National Midget Hall of Fame (2001). In addition to his USAC driving titles, he also has seven Sprint Car Owner championships as well as seven in the Silver Crown Series as an owner.[62]

Stewart frequently makes appearances on dirt tracks, appearing regularly at an ARCA race on dirt and at many prominent midget car events, USACs Turkey Night Grand Prix, and the indoor Chili Bowl Midget Nationals.

Along with Matt Kenseth, he has appeared at Madison International Speedway, a non-NASCAR half-mile track located in Wisconsin on Highway 138 between the cities of Oregon, WI and Stoughton, WI.

Stewart races 410 and 360 Dirt Sprint Cars about 50 times a year throughout the United States and Canada. On July 27, 2011, Stewart won his first ever World of Outlaws race at Ohsweken Speedway. As of October 7, 2014, Stewart has three career World of Outlaws main event victories. Stewart competes with the World of Outlaws, All-Stars, and IRA Sprint Car series when traveling between NASCAR races and on off weekends.

On August 9, 2014, Stewart competed in an evening sprint car race at Canandaigua Motorsports Park in Canandaigua, New York. About halfway through the race, Stewart bumped Kevin Ward Jr., causing Ward to lose control and spin out, into the wall. A full course yellow caution flag was displayed. Instead of waiting for race officials, an indignant Ward exited his vehicle and walked onto the track, gesticulating in defiance as Stewart approached. As Stewart approached under full course caution he hit Ward, impacting him with his right rear tire. Mortally injured when the right rear tire of Stewart's car struck him, Ward was flung 25 feet (7.6 m) across the track to his death.[63] Ward was transported by paramedics to Thompson Hospital but was pronounced dead on arrival,[64] due to "massive blunt trauma".[65]

The incident took place the night before Stewart was scheduled to race in the Cup Series' Cheez-It 355 at Watkins Glen International; however, Stewart decided not to compete in the event, and Regan Smith started in his place.[66] Stewart later released a statement "There aren't words to describe the sadness I feel about the accident that took the life of Kevin Ward Jr. It's a very emotional time for all involved, and it is the reason I've decided not to participate in today's race at Watkins Glen. My thoughts and prayers are with his family, friends, and everyone affected by this tragedy."[67]

The day after the incident, Philip Povero, sheriff of Ontario County, New York, told reporters "At this very moment, there are no facts in hand that would substantiate or support a criminal charge, or indicate criminal intent on the part of any individual."[68]

On August 15, 2014, NASCAR announced a rule change requiring that drivers who are involved in an accident and are unable to drive their cars back to pit road or the garage must remain in their vehicles until emergency crews arrive, except in an emergency situation (such as a fire or smoke caused by a blown engine).[69]

For the August 17, 2014 race at Michigan and the following one at Bristol, Stewart was replaced by Jeff Burton.[70][71] He returned at Atlanta, and was granted a waiver to maintain Chase eligibility despite missing three races (current Chase rules state that a driver must attempt to qualify for every race in order to be eligible). However, he failed to win at Atlanta or Richmond and thus was unable to qualify for the Chase.

Stewart gave a tearful interview when he returned to race in Atlanta, stating:

This is been one of the toughest tragedies I've ever had to deal with, both professionally and personally. This is something that will definitely affect my life forever. This is a sadness and a pain I hope no one ever has to experience in their life. That being said, I know that the pain and the mourning that Kevin Ward's family and friends are experiencing is something that I can't possibly imagine. I want Kevin's father, Kevin Sr., his mother Pam, and his sisters Christi, Kayla, and Katelyn to know that every day I'm thinking about and praying for them.

The racing community is a large family, as you guys know. Everyone's saddened with this tragedy. I want to thank all my friends and family for their support through this tough, emotional time. And the support from the NASCAR community, my partners, all of our employees has been overwhelming. I've taken the last couple weeks off out of respect for Kevin and his family and also to cope with the accident in my own way. It's given me the time to think about life and how easy it is to take it for granted. I miss my team, my teammates, and the other drivers very much and I miss being back in the race car. I think that being back in the car this week with my racing family will help me get through this difficult time.[72]

On September 24, 2014, a grand jury declined to indict Stewart on charges of manslaughter in the second degree and criminally negligent homicide. Following the decision, District Attorney Michael Tantillo stated that videos of Stewart's driving did not demonstrate any aberrational driving and that Ward was under the influence of cannabis with levels high enough to impair judgment.[73]

Ward's father, Kevin Ward Sr., wrote a letter vowing to "pursue to make all remedies for Kevin,"[74] implying the civil lawsuit they later filed. When Ward's family was informed that he had been high on cannabis, Ward Sr. wrote a letter that went viral on the internet, saying:

Tell me how a man the size of Kevin can make a sprint car turn to the right on impact. Tell me how a lap before (the incident) everything was fine, but the following lap was poor lighting. Tell me how a NASCAR star totally forgot what caution means. Maybe he should get a different headset so he is able to hear on the radio that the car in caution is up high, so go low. Or was he low until he rounded the corner and saw Kevin, Jr. standing up for himself?[75]

A couple days after the announcement of his exoneration by Ontario County (N.Y.) District Attorney Michael Tantillo, Stewart told The Associated Press, that "I know 100 percent in my heart and in my mind that I did not do anything wrong. This was 100 percent an accident."[76]

After a few years of going through the process of the wrongful death lawsuit filed by the Ward family, it was announced in April 2018, that the suit had been settled out-of-court, just a few weeks before the trial was scheduled to begin. The terms of the settlement were confidential.

Stewart is the owner of various open-wheel short track racing cars, most of them being sponsored by Chevrolet since 2007. He also owns and drives dirt super late models.

In the end of the 2008 season, Stewart was given a 50% stake in Haas CNC Racing, which became Stewart-Haas Racing in 2009. Haas CNC Racing, previously fielded the No. 66 and 70 cars, now fields the No. 4, 14, 10, and 41 as Stewart-Haas Racing. This decision involved parting ways with long-time crew chief Greg Zipadelli, sponsor The Home Depot, car No. 20, and car owner Joe Gibbs, all of which he had spent 10 years with. Stewart formerly drove the No. 14 owned by Gene and Margaret Haas, which is now driven by Chase Briscoe. He is the owner of the No. 10, driven by Aric Almirola. Additionally, the No. 4 and 41 cars of Kevin Harvick and Cole Custer were newly added by Stewart-Haas Racing in 2014. Harvick, in his first year with Stewart-Haas, won the Sprint Cup Championship in 2014. Stewart-Haas Racing switched to Ford in 2017.[77]

Stewart has won USAC car owner titles in the Silver Crown division in 2002 and 2003 with J. J. Yeley, in 2004 with Dave Steele and 2010 and 2011 with Levi Jones of Olney, IL. He also collected owner titles in USAC's National Sprint Car Series with Yeley in 2003 and Jay Drake in 2004. He also won an owner title in the USAC National Sprint Car Series in 2006 with Josh Wise and in 2007, 2009, 2010, and 2011 with Levi Jones of Olney, IL

Stewart's USAC midget and sprint cars carry No. 20 and No. 21, while his Silver Crown car carries No. 22.

Stewart has also won World of Outlaws Sprint Car Championships as an owner with Donny Schatz in 2008–2009, 2012, and 2014–2018. [78]The team was a two car operation with Schatz and Steve Kinser until Kinser's retirement in 2016.[79] The team currently competes full time in the World of Outlaws with Schatz.

Stewart purchased Eldora Speedway located near Rossburg, Ohio in late 2004 from Earl Baltes. Stewart is currently a co-owner of Paducah International Raceway near Paducah, Kentucky. He also co-owns Macon Speedway in Macon, Illinois along with Kenny Schrader, Kenny Wallace, and Bob Sargent.[80]

In January 2015, Stewart purchased the All Star Circuit of Champions from Guy Webb.[81][82] The purchase was Stewart's first foray into owning an entire racing series. In a separate agreement, Stewart announced that he had reached an agreement with the owners of the Renegade Sprint Series to merge with the All Star Circuit of Champions for the 2015 season under the All Star name.

The ASCoC is an American motorsports sanctioning body of Sprint Cars founded in 1970. The series sanctions 410ci sprint car races in Ohio, Indiana, Pennsylvania, Michigan, Illinois, Wisconsin, New York, and Florida.

In July 2020, Stewart and former NASCAR crew chief Ray Evernham formed the Superstar Racing Experience (SRX), a stock car series that will begin in summer 2021.[83]

Stewart owns a dirt late model Chevrolet Impala that carries No. 14 which he races frequently. He is also the owner of Custom Works, a company that manufactures radio controlled oval track cars, and has had a degree of success as a r/c racer himself.

Stewart is also the driving force behind the Sprint-sponsored "Prelude to the Dream" which features drivers from various sports driving late model dirt cars at Eldora Speedway. Since 2005 the "Dream" has showcased a who's who in NASCAR and NHRA, featuring such drivers as Kyle Busch, Jeff Gordon, Matt Kenseth, Jimmie Johnson, Tony Pedregon, and others. The inaugural race was won by Kenny Wallace, followed by Carl Edwards in 2006. As of late the race has been nicknamed "The Smoke Show" due to Stewart winning back to back to back since 2007. The events have raised over 4 million dollars for various NASCAR and driver charities including The Victory Junction Gang Camp.

Founded in 2003 by Stewart, the principal purposes of the Tony Stewart Foundation are to raise and donate funds to help care for chronically ill children, drivers injured in motorsports activities, and to support other charitable organizations in the protection of various animal species. The Tony Stewart Foundation will raise and donate funds to charitable interests, specifically those that support the aforementioned groups.[84]

• 1995, 2002 Hoosier Auto Racing Fans Driver of the Year[85]
• 2001 National Midget Auto Racing Hall of Fame inductee
• 2002 Hoosier Auto Racing Fans Hall of Fame inductee[86]
• 2002, 2005, 2011 Richard Petty Driver of the Year[87]
• 2003, 2006, 2012 Best Driver ESPY Award recipient[88]
• 2008 Legends of The Glen inductee[89]
• 2008 NASCAR Illustrated Person of the Year Award recipient[90]
• 2013 Myers Brothers Award recipient[91]
• 2016 Sonoma Raceway Wall of Fame inductee[92]
• 2018 Indianapolis Motor Speedway Hall of Fame inductee[93]
• 2019 Motorsports Hall of Fame of America inductee[1]
• 2020 NASCAR Hall of Fame inductee

With 49 career points-paying victories, Stewart is ranked thirteenth among the all-time NASCAR Cup Series winners; he is ranked ninth among those who have competed during the sport's modern era (1972–present).

Stewart is the all-time winningest Cup Series driver at the following tracks:

• Chicagoland Speedway (3)
• Homestead-Miami Speedway (3; tied with Greg Biffle)
• Watkins Glen International (5)

Stewart hosted a two-hour weekly radio show, titled Tony Stewart Live, broadcast on Sirius Satellite Radio.[94] Stewart co-hosted the show with Matt Yocum, and took listener calls. The show ran from 2007 to 2008.

• From 1999 to 2001, Stewart worked for Turner Sports as a guest analyst on one NASCAR Busch Series race per year, one of the earliest examples of a current Cup driver doing commentary for a lower series race. Stewart called the fall Charlotte race in 1999 and 2000 alongside Allen Bestwick, and the Watkins Glen race in 2001 alongside Mike Hogewood.
• In 2007, Stewart appeared in commercials for Subway with their spokesman Jared Fogle.[95]
• He in a 2008 Toyota commercial where the cars of Toyota Sprint Cup drivers, including Stewart's, are driven by kids with remote controls. When his kid driver spins his car out of control, he crawls out, yelling to his crew chief, "Zippy, run for your life!" Stewart then throws his helmet at his car.[96]
• Stewart appears in commercials as a member of the Coca-Cola Racing Family of drivers.
• In 2010, Stewart appeared in a commercial for the Burger King Steak House XT, which he endorsed. This video entered the Top 10 of the Ad Age/Visible Measures Top Viral Ad Chart on August 12, 2010.[97]
• On February 14, 2012, Stewart guest-starred on the ABC series Last Man Standing.[98]
• On March 17, 2013, he voiced himself in The Cleveland Show in the episode, "The Hangover Part Tubbs".[99]
• In 2013 and 2014, Stewart appeared as himself in a special series of McLaren's cartoon Tooned in partnership with Mobil 1.[100]

• EA Sports announced that Stewart would appear in person for the first time on the cover of NASCAR Thunder 2004 in late 2003,[101] his Home Depot Winston Cup car appeared on NASCAR 2001's cover.[102] He also appears on the North American cover of NASCAR 08.[103]
• Stewart is included in NASCAR 2011: The Game and NASCAR The Game: Inside Line.[104] On December 3, 2013, it was announced that he would appear on the cover of NASCAR '14.[105]
• In 2019, Stewart and his Stewart-Haas Racing drivers were featured on the NASCAR Heat 4 cover; he also appears as a playable driver and dirt team owner in the game's Career Mode.[106] The following year, he was included on the cover of NASCAR Heat 5's Gold Edition.[107]
• In 2020, Stewart partnered with Monster Games for Tony Stewart's Sprint Car Racing. The game, which features Stewart's All Stars Circuit of Champions, was released on February 14, 2020.[108]

• He appeared with Dale Earnhardt Jr. in the music video for 3 Doors Down's song "The Road I'm On".[109]
• Stewart is mentioned in the song "Glory" by Lil Wayne off his Free Weezy Album.
• Stewart is mentioned in the song "Slow Down" by Clyde Carson featuring The Team.
• He appeared in the 2005 film Herbie: Fully Loaded, along with other NASCAR drivers, having his car driven over by Herbie and being one of four cars who boxed Herbie in.
• Stewart is mentioned in Eminem's verse on the Shady Records "SHADY CXVPHER" video promoting the compilation album Shady XV, specifically referencing the Kevin Ward Jr. incident.[110]
• In K-pop group Blackpink's music video for "Ddu-Du Ddu-Du", group member Lisa is seen wearing a vintage Stewart jacket from when he raced for Joe Gibbs Racing.[111]
• Stewart is mentioned in the song "Really Got It" by Jerreau.
• While the song didn't use his name, Stewart's number 14 was referenced in the Brad Paisley song "Country Nation". At the time of the song's 2015 release Stewart was still driving the #14 car in NASCAR. Every driver referenced in the song (Stewart, Jeff Gordon, Dale Earnhardt, Jr. and Jimmie Johnson) have since retired from the sport.

(key) (Races in bold indicate pole position; races in italics indicate fastest lap)

¹ The VisionAire 500K was abandoned after three spectators were killed when debris from a crash on the track went into the grandstands.

(key) (Bold – Pole position awarded by qualifying time. Italics – Pole position earned by points standings or practice time. * – Most laps led.)

^* Season still in progress
¹ Ineligible for series points

(key) (Bold – Pole position awarded by qualifying time. Italics – Pole position earned by points standings or practice time. * – Most laps led.)

(key) (Bold – Pole position. * – Most laps led.)

(key) (Races in bold indicate pole position, Results are overall/class)