Bobby Bonilla

Bonilla became the Pirates' starting third baseman in 1987, but after committing 67 errors over his next two seasons, manager Jim Leyland moved him to right field.[8] There he formed a formidable combination alongside stars Barry Bonds and Andy Van Slyke and helped propel the Pittsburgh Pirates to two of their three straight National League Eastern Division titles from 1990 to 1992.

From 1986 to 1991, Bonilla had a .284 batting average, with 868 hits, 191 doubles, 114 home runs, and 500 runs batted in (RBIs). He led the league in extra base hits in 1990, and in doubles in 1991. Bonilla also won three Silver Slugger Awards and made the All-Star team four years in a row. On October 28, 1991, he became a free agent.

Bonilla became the highest-paid player in the National League at the time when he signed a 5-year, $29 million contract (equivalent to $52.8 million today) with the New York Mets on December 2, 1991.[9][10] The $6.1 million he received in 1992 was a record for a single season by a margin of $2.3 million.[11] However, his offensive production diminished somewhat, finishing with a .278 batting average, 91 home runs, and 277 runs batted in during his three-and-a-half-year tenure with the Mets. Despite this, Bonilla ended up participating in two more All-Star Games (1993 and 1995).

Bonilla's time with the Mets was marked by a contentious relationship with New York baseball media. In his introductory press conference after signing with the organization, he challenged them by stating, “I know you all are gonna try, but you’re not gonna be able to wipe the smile off my face.”[12] On another occasion, he called the press box during a game to complain about an error that he was charged with.[13]

Bonilla was acquired along with a player to be named later (Jimmy Williams on August 16) by the Baltimore Orioles from the Mets in exchange for Damon Buford and Alex Ochoa on July 28, 1995, and helped the Orioles to the American League Championship Series in 1996.[14][15]

Following the 1996 season, Bonilla was once again granted free agency, and signed with the Florida Marlins, reuniting with his old manager, Jim Leyland, where he helped the Marlins win the 1997 World Series. He returned to the Marlins for the 1998 season and batted .278 through 18 games.

On May 14, 1998, Bonilla was traded to the Los Angeles Dodgers, along with Manuel Barrios, Jim Eisenreich, Charles Johnson, and Gary Sheffield, in exchange for Mike Piazza and Todd Zeile. Bonilla spent the rest of the 1998 season with the Dodgers, batting .237, with seven home runs and 30 runs batted in.

In November 1998, the New York Mets reacquired Bonilla from the Los Angeles Dodgers in exchange for Mel Rojas. Again, his level of play did not measure up to expectations and he had numerous clashes with manager Bobby Valentine over lack of playing time. His tenure in New York culminated in an incident during the sixth game of the 1999 NLCS during which the Mets were eliminated by the Braves in 11 innings while Bonilla reportedly sat in the clubhouse playing cards with teammate Rickey Henderson.[16]

After his subpar 1999 season, the Mets released Bonilla, but still owed him $5.9 million. Bonilla and his agent offered the Mets a deal: Bonilla would defer payment for a decade, and the Mets would pay him an annual paycheck of $1.19 million starting in 2011 and ending in 2035, adding up to a total payout of $29.8 million.[2][17] Mets owner Fred Wilpon accepted the deal mostly because he was heavily invested with Ponzi scheme operator Bernie Madoff, and the 10 percent returns he thought he was getting on his investments with Madoff outweighed the eight percent interest the Mets would be paying on Bonilla's initial $5.9 million. As a result, the payout was a subject of inquiry during the Madoff investment scandal investigation when it came to light in 2008.[18]

Bonilla signed with the Braves in 2000 and played a mostly uneventful 114 games for them. He achieved his highest batting average (.255) since the 1997 season, although he hit only five home runs, a far cry from his career high of 34.

In 2001, he was signed by the St. Louis Cardinals, but injuries reduced his playing time. He played his final game on October 7, 2001, and finished the season with a .213 average, 37 hits, five home runs, and 21 runs batted in. He retired after the season finished citing "injuries and reduced playing time" as the main reason for his decision.[19]

Overall, Bonilla finished his career with one championship, six All-Star appearances, 2,010 hits, 287 home runs, 1,173 runs batted in, and a career .279 batting average.

In February 1992, Bonilla and his wife Millie started the Bobby and Millie Bonilla Public School Fund with $35,000. The fund benefits schools attended by Bonilla and his wife, by contributing $500 for every run he batted in for the Mets.[5][21] Bonilla also participated in other charity events, like the Players Trust All-Star Golf Tournament, organized by Dave Winfield and Joe Mauer in 2014.[22]