Michael Waltrip

According to his autobiography Blink of An Eye, Waltrip's career started at age 12. When he was 12 he phoned his older brother Darrell Waltrip, who was out racing in the 1978 Daytona 500 and asked Darrell to help him build a career in NASCAR. Darrell, however, claimed he had no time to help him and advised that Michael focused on school. When Michael asked his dad for help, his dad ignored his requests. With none of his parental figures helping him, Michael built his racing career all by himself with influence & help from his older brother Bobby Waltrip, who was very close to him in childhood. He began building a career by racing go-karts at carnivals and various racing clubs around his hometown. He won many races and, thanks to Bobby's help, was noticed by rising hotshot star Dale Earnhardt. When Waltrip moved out of his house, he moved in with Kyle Petty and then he ultimately ended up living with Richard Petty as a roommate. When Michael explained to Petty that he was going to try the Busch Series (now the Xfinity Series) to build his NASCAR career, Petty told Michael he was "wasting his time" and advised that Michael should immediately go for the Cup Series ride.

1989 car

Waltrip's stock-car career got off the ground in 1981, when he captured the Mini-Modified division track championship at Kentucky Motor Speedway. A year later, Waltrip entered the Goody's Dash Series, where he won the series championship in 1983 and was voted the circuit's most popular driver in 1983 and 1984.

Waltrip made his Cup debut in 1985 in the Coca-Cola 600 at Charlotte driving for Dick Bahre. He finished 28th in that race and finished 57th in the series standings after just 5 starts. His brother Darrell won the race. At the same time, Waltrip got confronted by Earnhardt, who questioned a previous move early in the race in which Waltrip nudged him out of the way and Dale responded by flipping the bird. Despite this incident, Earnhardt and Waltrip agreed to disagree over the move and remained friends.

This is what was salvaged from Waltrip's 1990 Kool-Aid sponsored Busch Series car after his accident at Bristol.[1]

In 1986, driving the No. 23 car for Bahari Racing, Waltrip finished second in the Rookie of the Year standings to Alan Kulwicki on the strength of a pair of 11th-place finishes at Martinsville and Pocono. The following season, he posted his first career Top 10 finish when he ended up 10th in Martinsville's spring race. In 1988, Waltrip began running Busch Series events, making 5 starts for his brother's team. He took the checkered flag for the first time at Dover in his 4th start. In 1989, he had his first top-five finish in the No. 30 Country Time Lemonade/Kool Aid-sponsored Pontiac.

For Waltrip, 1990 was memorable for a horrific crash at Bristol in the spring on the 170th lap of the Budweiser 250, where he destroyed his Busch Series Pontiac Grand Prix. After making contact with Robert Pressley in the No. 59, he hit a gate that was in the outside wall at the exit of turn two. The gate was used to allow vehicles in and out of the infield because the track did not have a tunnel. The impact broke the gate, and Michael went head-on into the end of the wall, disintegrating the car on impact and collapsing the car into itself. Onlookers were sure that Waltrip was severely injured, perhaps fatally, because of how massive the impact was and his brother Darrell rushed to the wreck fearing the worst. Amazingly, Waltrip survived the accident and he only suffered cuts, soreness, and bruises in the wreck.[2] After Mike Harmon had an almost identical impact several years later (and also amazingly walked away), the gate was moved down to just before the entrance of Turn 3, thus lessening the chance of a car hitting it because cars are diving away from the wall at that point. Later, when asked about the crash by Ken Squier, he replied saying he had "some contusions and a little bit of confusion" and ended with "Hope we did a good job for Kool-Aid." Years later, Waltrip said that at first, he thought that Pressley wrecked him on purpose, and thought about fighting him after the incident before thinking better of it.[3]

In early race lineups, Waltrip was referred to by broadcasters as "Mike Waltrip" or Darrell's little brother. It wasn't until 1991 that he began being referred to in racing lineups as Michael (Waltrip).

Waltrip driving for Bahari in 1994

In 1991, he gained new sponsorship from Pennzoil and won the Winston Open, as well as his first two career pole positions. He came close to winning the 1991 TranSouth 500 at Darlington, but a jammed air hose on his final visit to the pits caused his stop to last 37.4 seconds, costing him the victory. He stayed with the Bahari team until the end of 1995, when he was replaced by rookie Johnny Benson. He joined Wood Brothers Racing to drive their No. 21 Citgo-sponsored Ford. He won the 1996 edition of The Winston after capturing the last transfer spot in The Winston Open. After posting one top five finish over a period of three years, and missing his first race since 1986 at the 1998 Dura Lube/Kmart 500, Waltrip departed the Wood Brothers at the end of 1998 to drive the No. 7 Philips-sponsored Chevrolet for Mattei Motorsports, posting three Top 10 finishes and ending that season 29th in points. However, mid-season the ownership of the team transferred from Mattei to Ultra Motorsports and Jim Smith. The next season, Nations Rent replaced Philips as the sponsor & Waltrip moved up to 27th in points but only finished in the Top 5 once, causing him and the team to part ways at the end of the season. Waltrip would later say in his 2011 book, In the Blink of an Eye, that 1999 and 2000 were the most disappointing years of his racing career and he began to lose faith that he would win a race.

Waltrip was hired by Dale Earnhardt to drive his team's new No. 15 NAPA Auto Parts-sponsored Chevrolet Monte Carlo entry, Waltrip drove for Earnhardt in the Busch Series in 1989 and 1994. In his first race with the team, the 2001 Daytona 500, Waltrip broke his streak of 462 consecutive Cup races without a victory and won his first career points-paying Cup race. His teammate Dale Earnhardt Jr. finished in 2nd. However, the win itself was largely overshadowed by Earnhardt, Sr.'s fatal crash on the last lap. In the movie The Day: Remembering Dale Earnhardt, Waltrip said that Earnhardt let him in line late in the race, which allowed him to take the lead, noting that Earnhardt "never let anyone in line". This presumably is because Earnhardt wanted Waltrip and Earnhardt Jr. to finish in the Top 2 spots, as both were members of his team. Waltrip was not aware of the severity of Earnhardt's crash until over 30 minutes after the end of the race when he was celebrating in victory lane. Ken Schrader, after having been treated and released from the infield care center following the crash (his car was hit by Earnhardt's during the crash), informed Waltrip that Earnhardt had been taken to Halifax Medical Center, 2 miles (3.2 km) from the speedway, where Earnhardt was pronounced dead at 5:16 PM EST.

Waltrip would later say in his book, and a 2019 podcast episode with Earnhardt Jr., that in the aftermath of the tragedy, he and the No. 15 team pushed forward to continue Earnhardt's legacy, "Because we knew we had to." However, his results slumped in the aftermath of the disaster, and he realized after 6 races that he was "not in a good place."[4] By June 2001, his crew chief, Scott Eggleston, departed the team and was replaced by longtime DEI director Steve Hmiel.[5]

Waltrip did not have another Top 10 finish that season until returning to Daytona in July in the Pepsi 400, where he finished 2nd while holding off the field as teammate Earnhardt Jr. won his first plate race. Earnhardt Jr.'s Pepsi 400 finish was emotional to the entire DEI team and when Earnhardt Jr. did his burnout on the infield grass, Waltrip pulled up alongside him. Waltrip would also have a second-place finish at Homestead with Bill Elliott winning, and finished 24th in the standings.

The next season, Waltrip won the second Gatorade Duel. His next top ten finish would be a second-place finish at Talladega, where he and Earnhardt Jr. combined to lead more than two-thirds of the race, with Earnhardt Jr. taking home his second of four straight wins at Talladega. The following week, Waltrip finished tenth at Auto Club. He had eighth-place finishes in the Coca-Cola 600 at Charlotte and the first Pocono race, and fourth place in the first Michigan race. He picked up his second career win at the Pepsi 400 at Daytona. After a ninth-place finish at Watkins Glen, and eighth-place finishes at New Hampshire and Talladega, Waltrip finished 14th in the points standings.

In 2003, Waltrip won a rain-shortened Daytona 500 and also took victory at the EA Sports 500 at Talladega (his only non-Daytona win), while running in the top-five for most of the season before falling back to 15th in points. Of trivial note, Waltrip won the first three NASCAR on Fox races at Daytona (2001 and 2003 Daytona 500s, and the 2002 Pepsi 400) with Michael's brother Darrell in the broadcast booth. His Talladega win was also his only win at a NASCAR on NBC race.

In 2004, Waltrip went winless and dropped five spots in the standings. In 2005 Waltrip only had seven top tens and one pole. It included a runner up at Phoenix despite hitting the wall on the next to last lap. He had an incident with Robby Gordon at New Hampshire. After Waltrip intentionally wrecked Robby Gordon and spun as a result, Gordon furiously tried to back his damaged racecar into Waltrip's. When Gordon failed to hit Waltrip's car with his own, he climbed out of his racecar and threw his helmet at Waltrip's driver side door. Waltrip repeated the words Gordon said the previous year in another helmet-tossing incident: "He just threw a helmet at my car." Waltrip was fined $10,000 after he gestured at Gordon for the damage on his car from the helmet, but he and Teresa Earnhardt appealed and the fine was overturned after a short investigation proved the charge false. Gordon however was fined $50,000 and put on probation for the rest of the year after he was discovered to have said "You know everybody thinks Michael is this good guy. He's not the guy he acts he is. The caution was out, and he wrecked me, and he's a piece of shit." Waltrip and Gordon conferred later on, apologized, and continued their careers. After the 2005 season, Waltrip left DEI for Bill Davis Racing.

Michael Waltrip's No. 55 NAPA Dodge (right) in 2006

On January 20, 2006, Waltrip and Doug Bawel, who owned Penske Racing's No. 77 car in 2005, announced the forming of Waltrip-Jasper Racing.[6] Because Waltrip was under contract with Bill Davis Racing, they reached a deal with BDR to oversee and supply the new team. Waltrip-Jasper fielded the No. 55 NAPA Auto Parts Dodge in the 2006 Nextel Cup Series, driven by Waltrip, with Bawel as listed owner, and Davis as a team executive. Bawel had a guaranteed starting spot in the first five races of 2006 by virtue of the No. 77 finishing 34th in the 2005 owner points, although Bawel was shutting down his team and needed a driver to pick up his team's owner points. This arrangement enabled Waltrip to make the first five races in 2006 without qualifying on time. After the first five races this was unnecessary. Waltrip failed to qualify for the first time since 1998 at the Coca-Cola 600. He bought a slot from the No. 74 McGlynn Racing Dodge from Derrike Cope to drive in the race and to keep his streak of 262 consecutive races.[7] Waltrip ended up missing three races total in 2006 and did not have a top-ten finish. This was attributable to BDR's lawsuit with Dodge, which meant the team did not receive manufacturer support for Waltrip or teammate Dave Blaney.

Waltrip left Bill Davis Racing to form his own Nextel Cup team in 2007.

Waltrip moved his Busch Series team, Michael Waltrip Racing, to the Cup Series full-time for the 2007 season. He hired Dale Jarrett and David Reutimann to race in the three car operation. Reutimann in the No. 00, Jarrett in the No. 44, and Waltrip in the No. 55. Waltrip was listed as the owner of the No. 44 and No. 55, while his wife Buffy was listed the owner of the No. 00.

After the first round of qualifying for the 2007 Daytona 500, NASCAR inspectors found evidence in the engine intake manifold that Waltrip, Reutimann and Jarrett's teams had used an illegal unspecified oxygenate fuel additive to increase performance. NASCAR confiscated the cars, forcing Waltrip, Reutimann and Jarrett to move to back-up cars for the Daytona 500. On February 14, 2007, NASCAR officials announced at a press conference the penalties that would be levied: Bobby Kennedy (Director of Competition for Michael Waltrip Racing) and David Hyder (Waltrip's crew chief) were removed from Daytona International Speedway, and suspended indefinitely.[8] David Hyder was also fined $100,000 and was placed on a leave of absence, eventually to be released by the team in April. Waltrip, Reutimann and Jarrett was docked 100 driver points and Waltrip and Buffy were docked 100 owner points each. Waltrip, Reutimann and Jarrett's initial qualifying times were disallowed, but Waltrip and Reutimann were permitted to attempt to qualify by racing a backup car in their Gatorade Duel's qualifying race for the Daytona 500. Jarrett would qualify using his Past Champions provisional from his 1999 title, but was also permitted to race a backup car in his Gatorade Duel.[9] Waltrip's interim crew chief was announced as Scott Eggleston, who was Waltrip's former crew chief in 2001.[10] After a 30th-place finish in the Daytona 500, Waltrip became the first driver in series history to go into the second race of the season with a negative number of points (−27). Waltrip failed to qualify for the next eleven races following the Daytona 500, so he maintained his negative point total for almost 4 months. He qualified for the thirteenth race of the season at Dover and finished 28th, moving his point total above zero to 52 points.

On Saturday, April 7, 2007 he fell asleep behind the wheel of his Toyota Land Cruiser which overturned and hit a utility pole. Waltrip crawled out from the car suffering only minor cuts. There was no Nextel Cup race held that weekend. He was charged with reckless driving and failing to report an accident.[11][12]

After failing to qualify for the Pocono 500 in June, Waltrip bounced back the following week by finishing 10th at the Citizens Bank 400 in Michigan.

During the summer, Waltrip decided to make changes to the No. 00 and No. 55, which both sat outside the top 35 in owners points. He hired Terry Labonte, who held an automatic qualifying spot with his Past Champions provisional from titles in 1984 and 1996, to take over Waltrip's No. 55 at Infineon Raceway, Watkins Glen International, and Indianapolis Motor Speedway. Waltrip also hired P. J. Jones, a road course ringer, to take over David Reutimann's No. 00 at Infineon and Watkins Glen.

In October 2007, prior to the 2007 Bank of America 500. Dale Jarrett announced his retirement from points racing after the 2008 Food City 500, Waltrip decided to put David Reutimann (No. 00 driver) to take over the No. 44. Jarrett's final race was the All-Star race in May 2008.

On October 6, 2007, Waltrip won the pole for the UAW-Ford 500 at Talladega Superspeedway, the first restrictor plate race to be run with the Car of Tomorrow.[13] He finished 25th after a wreck, but bounced back the next week at Charlotte Motor Speedway with his second top-10 finish of the season.

Waltrip's 2008 car at Daytona

In 2008, Michael Waltrip Racing underwent a change following the disappointing 2007 campaign. Waltrip welcomed business owner Robert Kaufmann, owner/founder of the Fortress Investment Group and was made an equal partner and got more aid with real estate developer Johnny Harris buying into the team during the 2007 off-season. Former Cup owner Cal Wells was brought to MWR to oversee day-to-day operations, Dale Jarrett No. 44 retiring from points racing after the 2008 Food City 500, David Reutimann starting the season in the No. 00 then taking over Jarrett's No. 44, while Michael McDowell took over Reutimann's No. 00. Waltrip entered three full-time cars for 2008 David Reutimann/Michael McDowell/Mike Skinner/Kenny Wallace/A. J. Allmendinger and Mike Bliss No. 00, Dale Jarrett/David ReutimannNo. 44 and Waltrip No. 55. On February 10, 2008, Michael qualified second for the 50th running of the Daytona 500, which guaranteed him a second place start in the race. Waltrip started the race with "gold wheels" on his car in tribute to the golden anniversary of the Daytona 500; after the race the wheels were signed and sold to benefit NASCAR charities.[14] After leading the first two laps, he was not a factor in the race and finished 26th. Waltrip finished second at New Hampshire's Lenox Industrial Tools 301. He made his 1,000th NASCAR touring series start at Atlanta in October. He is second to Richard Petty in most career starts spanning all of the top divisions in NASCAR.

However, Michael McDowell struggled to keep the car in the Top 35 in owner points, which is necessary for automatic qualification into each race, and Waltrip replaced him with Mike Skinner, Kenny Wallace, A. J. Allmendinger and Mike Bliss in an effort to reclaim a Top 35 spot. In October 2008, MWR transferred its third team to the No. 47 Toyota of JTG Daugherty Racing, driven by Marcos Ambrose, and discontinued the No. 00 team for the balance of the season.

At the end of 2008 MWR sold the No. 44 to Richard Petty Motorsports and contracted to two cars with David Reutimann moving back to the No. 00, Waltrip in the No. 55.

Waltrip in 2008

Waltrip entered two full-time cars for 2009 David Reutimann No. 00, Waltrip No. 55. In early 2009, Waltrip announced that he would be sharing the No. 99 NNS Aaron's dream machine with David Reutimann and Scott Speed during the season. On May 25, 2009 Waltrip scored his first win as an owner in Sprint Cup Series competition in the Coca-Cola 600, with David Reutimann winning the event.

In the 2009 season, Waltrip garnered two top ten finishes (Daytona and Talladega) He came within a few laps of winning his third Daytona 500 as he was moving forward when the race was called for rain. He ended up seventh.

Waltrip decided to skip the road courses (Infineon Raceway and Watkins Glen International) handing it over to Patrick Carpentier to get the No. 55 back in the top 35 owners points.

On July 7, 2009 Waltrip announced he would be driving part-time in the 2010 season starting with the Daytona 500.[15] Waltrip also announced Martin Truex Jr. will take over Waltrip's car as the No. 56 NAPA Auto Parts Toyota full-time in 2010, using the No. 55 owners points.

In 2010, Waltrip announced that he would only be racing at the Daytona 500 unless more sponsorship was found; Waltrip drove the No. 51 for the 2010 Daytona 500. Waltrip entered two full-time cars for 2010 No. 00 David Reutimann and No. 56 Martin Truex Jr., with Reutimann and Truex Jr. running the full schedule, Waltrip ran 6 races Daytona 500 (No. 51 MWR), Food City 500 (No. 55 Prism), Aaron's 499 (No. 55 Prism), Heluva Good! Sour Cream Dips 400 (No. 55 Prism), Toyota/Save Mart 350 (No. 55 Prism) and AMP Energy Juice 500 (No. 55 MWR). Waltrip qualified 21st on Daytona Pole qualifying day. This was not fast enough to get in the race on speed, however. He then wrecked out of the first qualifying race. Waltrip was able to gain a spot in the starting grid when driver Scott Speed raced to make the 500 using his qualifying time in the second qualifying race, giving Waltrip the 43rd place starting position. He finished in a respectable 18th place. Since then, Michael has started the No. 55 Prism Motorsports entry at Bristol, finishing 41st. Waltrip qualified for the Aaron's 499 at Talladega Superspeedway and raced his way to the lead early, but wound up finishing 39th after "The Big One" on lap 84 of the race. It was announced in May that Waltrip would pilot the Toyota Sponsafier winning paint scheme on June 20 at Infineon Raceway in Sonoma, CA, but he failed to qualify. Waltrip also ran the Amp Energy 500 in a Michael Waltrip Racing fielded No. 55 Toyota where he would lead three laps and finish 28th.

Waltrip and his business partner Rob Kaufmann have entered various GT endurance races, participating in the Dubai 24 Hours and also the 24 Hours of Spa, driving a Ferrari F430 GTE for Italian team AF Corse in both races. Waltrip, Kaufmann, and the AF Corse team finished 5th overall and 3rd in class at Spa, clinching a podium spot.

In 2011, Waltrip announced that he would attempt to make his 25th consecutive Daytona 500 start driving the No. 15. Waltrip retained his drivers for 2011 No. 00 David Reutimann in the No. 00 and No. 56 Martin Truex, Jr. in the No. 56, both of whom would run the full schedule. As well as the Daytona 500, Waltrip ran three races that year: the Aaron's 499, the Quaker State 400, and the Good Sam Club 500. Aside from the Sprint Cup event at Daytona, Waltrip also competed in the Camping World Truck Series and Nationwide Series races there. He captured an emotional win in the NextEra Energy Resources 250, which came 10 years to the day of the death of Dale Earnhardt and his first Sprint Cup Series victory. The victory also made Waltrip the 22nd driver to win a race in all three NASCAR national touring series. He followed up his Friday night win with a solid 9th-place finish in the Nationwide Series race the next day. On Sunday afternoon, as part of the commemoration of the tenth anniversary of Dale Earnhardt's death in the 2001 Daytona 500, (which Waltrip won) Waltrip drove a replica of the No. 15 NAPA Auto Parts-sponsored car that he drove at the time. However, Waltrip finished 40th in the race after getting caught up in an early wreck that eliminated 14 cars. For the rest of 2011, Waltrip said he was working on plans to attempt the Sprint Cup Inaugural event at Kentucky Speedway in July, along with his first Le Mans start with AF Corse.[16] He ran in the 2011 24 Hours of Le Mans in June in one of the AF Corse entered Ferraris. The car he co-drove with Robert Kauffman and Rui Águas completed 178 laps before retiring, finishing 38th overall. On September 29, 2011, it was announced that Waltrip would be replacing Jeff Hammond in the FOX's Hollywood Hotel on NASCAR on Fox beginning with the Daytona 500 in 2012 with Chris Myers and his brother Darrell Waltrip.[17]

At the end of 2011, Waltrip hired Clint Bowyer to drive the No. 15 in 2012. On November 4, 2011, MWR announced that David Reutimann would not return as driver of the No. 00 for 2012 so Waltrip changed the number to No. 55 in honor of Aaron's 1955 founding and he hired Mark Martin and Brian Vickers to co drive with Waltrip in 2012 and 2013

In January, he was confirmed as a driver for AF Corse Ferrari in the inaugural season of the FIA World Endurance Championship.[18] Four weeks before the Daytona 500, Waltrip and Rob Kaufmann entered the 2012 Rolex 24 at Daytona. After a series of mechanical problems and off course excursions, Waltrip, Rob Kaufmann, Rui Águas, and Travis Pastrana never gave up and pressed on to finish 22nd in GT and 35th overall.

In early February it was announced that Waltrip would attempt to qualify for the 2012 Daytona 500 for Hillman Racing, driving the No. 40 Toyota with sponsorship from Aaron's.[19] He failed to qualify for the race, crashing in a single-car incident in the first Gatorade Duel race.[20]

On May 6, Waltrip qualified for the 2012 Aarons 499 at Talladega Superspeedway and led several laps before finishing 19th.

He also qualified for the fall Talladega race. On the last lap, Waltrip was running 5th when he jumped to the bottom lane and made a move for the lead to try to win heading into turn 4 with drafting help from Casey Mears. In turn 4, Tony Stewart tried to block Waltrip but underestimated Waltrip's speed. Waltrip tapped Stewart, and went up into the tightly bunched pack, collecting 23 cars, while Stewart flipped over once and slid on his side airborne and pushed by the wrecking field. Waltrip finished 25th.

Waltrip competed in the 2013 Denny Hamlin Short Track Showdown

Waltrip entered the 2013 Daytona 500 driving the No. 30 Toyota for Swan Racing,[21] which was changed for Daytona to the No. 26 as a charity car to raise funds for victims of the Newtown, Connecticut shooting. At his Budweiser Duel, Waltrip ran as high as close to the front, but faded back in the final laps. He ultimately finished 15th, but it was enough to grab the final transfer spot for the Daytona 500. At the Great American Race, Waltrip led four laps and finished 22nd in the race.[22] He also finished in the top 5 at all other races (3 others) too.

In his first race in the No. 55 for the season at Talladega, Waltrip finished fourth. He also ran at Daytona in July and finished 5th.

On September 12, 2013, NASCAR penalized Michael Waltrip Racing for intentionally manipulating the outcome of the Federated Auto Parts 400. As a result, NAPA Auto Parts pulled its sponsorship of the team at the end of the year, forcing Waltrip to release Martin Truex Jr. from his contract.

After originally announcing that he would field a part-time car for semi-retired Jeff Burton, plans changed when Waltrip sold the #56 team to investors of Identity Ventures who started a satellite team for MWR. Waltrip ran 4 races for Identity Ventures Racing owned by Jay Robinson, Mark Bailey and James Hamilton.

Waltrip ran the Daytona 500, Aaron's 499, Coke Zero 400 and GEICO 500. At Daytona in Speedweeks, Waltrip was collected in a last-lap pileup caused when Jimmie Johnson ran out of gas on the final lap. Waltrip nonetheless made it into the race. He crashed on lap 144 and finished 41st. He finished 25th at the Aaron's 499 at Talladega.

For both races, he eschewed working with regular Identity Ventures Racing crew chief Scott Eggleston, with whom he had won his first Daytona 500, and instead paired himself with Chad Walter. At the summer Daytona race, Waltrip finally decided to work with Eggleston, and ended up getting his first top-20 in over a year. However at Talladega in October, Waltrip again worked with Walter and did pick up another top-20. Identity Ventures Racing closed up shop after the season was over.

Waltrip returned to driving for his own team, piloting the No. 55 at both Daytona and Talladega in the spring. Waltrip skipped the summer Daytona race, but returned at Talladega in the fall, running a third MWR entry after leasing the owner points from the No. 98 of Premium Motorsports.

On February 4, Waltrip announced he would return to the Daytona 500, driving the No. 83 Camry for BK Racing.[23] Waltrip drove the No. 55 Camry for Premium Motorsports at Talladega in April with Peak BlueDEF as sponsor. Waltrip skipped again the summer Daytona race.

Waltrip announced he would run the Daytona 500, driving the No. 15 Aaron's, Inc. Camry for Premium Motorsports. It would be his final start in NASCAR-sanctioned racing.[24] Waltrip started 32nd out of the 40 car field, avoiding several large wrecks to end his NASCAR career with an eighth-place finish.[25]

Waltrip appeared on the two-part April 30, 2009/May 7, 2009 episode of My Name Is Earl entitled "Inside Probe."[31]

He works as a color commentator for NASCAR on Fox, covering the Xfinity Series since 2015 and the Truck Series since 2004.

On September 4, 2014, Waltrip was announced as one of the celebrities who would participate on the 19th season of Dancing with the Stars. He was paired with professional dancer Emma Slater. They were eliminated on November 3, 2014.[32]

On the December 2, 2019 episode of WWE Raw, Waltrip put on a referees uniform and helped Kyle Busch defeat R-Truth for WWE 24/7 Championship[33]

Waltrip wrote a book published in 2011 called In the Blink of an Eye: Dale, Daytona, and the Day that Changed Everything. It became a New York Times best-seller.[34] A documentary film adaptation, Blink of an Eye, was released in 2019.[35]

In a race in the early 1990s, Waltrip hit driver Dave Marcis while he was still in his car, punching him in the mouth and cutting his lip open, and was fined $500 for his actions.[36]

In 1995 at Michigan International Speedway, Waltrip also hit driver, Lake Speed. Waltrip hit Speed twice on national television,[37] while Speed was strapped in his car. Waltrip was fined $10,000 for his actions.

Waltrip had a much-publicized feud with fellow Kentucky-man Jeff Green, then driver of Petty Enterprises No. 43 Cheerios/Betty Crocker Dodge Charger in the early part of the 2005 season, which came to a head during races at Martinsville and Darlington, where Green and Waltrip wrecked each other on several occasions.[38] The feud went back to 2002, when racing for the win at Rockingham caused both to lose control of their cars, allowing Jamie McMurray to win his second straight Busch Series race. After Waltrip retaliated against Green late in the Darlington race, NASCAR penalized Waltrip with a 1-lap penalty. Following the race, NASCAR brought Green and Waltrip together and warned them to avoid future incidents.

In the 2005 Sylvania 300, Waltrip wrecked Robby Gordon's No. 7 Jim Beam Chevrolet after the yellow flag had come out. The angered Gordon got out of his totaled car and threw his helmet at the No. 15 car as it was passing by. When TNT interviewed him about the crash he stated "You know Michael, everyone thinks Michael's this good guy. He's not the good guy he acts he is. The caution was out and he wrecked me and he's a piece of shit."[39] TNT apologized for the incident on both drivers' behalf, and both Gordon and Waltrip were required to meet with NASCAR officials after the race. Gordon was fined $50,000 and docked 50 drivers' points. Waltrip was also penalized, but the penalties were overturned on appeal. Gordon and Waltrip ultimately decided to auction the helmet for the benefit of the Harrah's Employee Relief Fund, a fund that provides aid to Harrah's employees displaced by Hurricane Katrina.[40]

In 2008, Waltrip made contact with Casey Mears with 46 laps to go resulting in Mears successfully passing him. As a reply, Waltrip rushed up to Mears, locked his hood on Mears' damaged car and tried to push it around through a struggle lasting over 4 seconds. Eventually Mears crashed, and soon after, NASCAR parked Waltrip as a punishment.[41]

In the 2008 Sharpie 500, an irate Clint Bowyer, who was involved in a wreck involving Waltrip, said "Michael Waltrip is the worst driver in NASCAR, period! Could not believe NAPA (his primary sponsor) signed him back on!" However, Bowyer made it up with him after 2008 and eventually joined Waltrip's race team in 2012.[42]

In 2007, Waltrip had his No. 55 Toyota confiscated by NASCAR officials after inspectors found an odorless, Vaseline-like substance in the car's engine. Later in the week, NASCAR handed down punishment to Michael Waltrip Racing, which included the ejection of team vice president of competition Bobby Kennedy and Crew Chief David Hyder from the garage at Daytona. Hyder was also fined $100,000, the largest fine ever handed down by NASCAR (until Kurt Busch was penalized for a pit road incident). Waltrip himself was penalized with a loss of 100 driver points and his qualifying time from pole day on Feb 11 was thrown out. Elizabeth Waltrip, Michael's wife and the official owner of his car, was also docked 100 owners points. The substance found in the vehicle's fuel was referred to as "rocket fuel", later determined to be Sterno.[43]

In the 2013 Federated Auto Parts 400, the final race before the Chase for the Sprint Cup, Waltrip's team was penalized with the biggest penalty in NASCAR’s history. In the race, MWR's Clint Bowyer spun out with 7 laps left after radio conversation hinting at an order to do so, and Brian Vickers was ordered to pit because the team "needed one more point". Following an investigation by NASCAR, the team was fined $300,000, stripped 50 driver points and 50 owner's points for each team, indefinitely suspended team vice-president Ty Norris and put every MWR crew chief on probation until December 31. With the points loss, Truex missed the Chase, which put Ryan Newman back in the wildcard spot. Waltrip stated as a reaction to the penalties that "I want to sincerely apologize to NASCAR, our sponsors, fans, and fellow drivers who were disappointed in our actions. We will learn from this and move on."[44]

On April 11, 2007, Waltrip was charged with reckless driving and leaving the scene of the accident after crashing his car into a telephone pole.[45]

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