Before establishing himself as a six-time All Star, Bonilla had to overcome long odds just to make it to the big leagues. After not being drafted out of Lehman High School in the Bronx, Bonilla was signed by the Pirates as an amateur free agent in 1981. He struggled through each of his first two seasons in rookie ball, hitting a combined .225. A broken leg limited Bonilla to just 39 games at Class A in 1985.
Left unprotected by the Pirates, Bonilla was snatched up by the Chicago White Sox in the Rule 5 Draft. But his tenure on the South Side was short, as the Pirates brought Bonilla back to Pittsburgh with a trade the next summer.
Surrounded by a group of talented young players, including Barry Bonds, Andy Van Slyke and Doug Drabek, and new Bucs skipper Jim Leyland, Bonilla's fledgling career took off in 1987. In his first full season with Pittsburgh, Bonilla batted .300 and became the first Pirates player to ever hit home runs from both sides of the plate in a game.
In 1988, Bonilla collected 100 RBIs for the first of four times in his career, earned his first of three Silver Slugger Awards and beat out Phillies Hall of Famer Mike Schmidt as the starting third baseman on the National League All-Star team. A year later, he earned his second All-Star berth and posted double-digit totals in doubles, triples and home runs.
In 1990, Bonilla was a key cog in Pittsburgh's first division championship team since 1979. He batted .280 with 32 home runs and a career-high 120 RBIs, notched his second Silver Slugger Award and finished as the runner-up to Bonds in the NL MVP balloting. Bonilla made his fourth straight appearance on the NL All-Star team in 1991, his final season with Pittsburgh, and finished third in the MVP balloting to Atlanta's Terry Pendleton and Bonds while helping to lead the Bucs to their second of three consecutive appearances in the NL Championship Series.
As one of the most sought-after free agents on the market in the winter of 1991, Bonilla signed a five-year, $29 million deal with the New York Mets. Although Bonilla was twice an All-Star during his three-plus seasons with New York, he never seemed to be able to live up to the lofty expectations of his hometown fans.
Bonilla enjoyed a career rebirth of sorts with Baltimore in 1996, when he hit .287 with 28 home runs and 116 RBIs while helping the Orioles reach the American League Championship Series.
Bonilla was reunited with Leyland in Florida in 1996. And after coming up short in his three previous Championship Series appearances, Bonilla finally got a shot at the World Series after the Marlins topped the Braves in the NLCS. He struggled at the plate in the first six games of the Fall Classic against the Indians before coming up big in Game 7 by hitting a home run in the seventh inning and sparking the winning rally with a single in the 11th inning.
Bonilla wrapped up his career with the St. Louis Cardinals in 2001 after making two more postseason appearances with the Mets in 1999 and the Braves in 2000.
In all, Bonilla collected 2,010 hits, clubbed 287 home runs and drove home 1,173 runs while posting a .279 lifetime batting average in 2,113 games.
"He had a very good career," Leyland said. "He was a force offensively, he played hard and he was always a great personality for the clubhouse.
"He was a treat to manage. I was very close to him and I still am."