Roberto Martin Antonio Bonilla was born on February 23, 1963.
Bobby Bonilla graduated from Herbert H. Lehman High School in the Bronx in 1981 and briefly studied computer science at New York Institute of Technology.
Bobby Bonilla began playing winter league baseball with the Mayagüez Indians in Puerto Rico in 1984.
During spring training in 1985, Bobby Bonilla suffered a broken right leg after colliding with teammate Bip Roberts, temporarily halting his progress in the Pirates' farm system.
Bobby Bonilla made his Major League Baseball debut with the Chicago White Sox in 1986.
From 1986 to 1991, Bobby Bonilla enjoyed a successful period with the Pittsburgh Pirates, marked by impressive batting statistics and multiple All-Star selections.
The Chicago White Sox selected Bobby Bonilla in the Rule 5 draft during the 1985-1986 offseason. However, he was later traded back to the Pittsburgh Pirates.
Initially a third baseman, Bobby Bonilla transitioned to right field in 1987 under the guidance of manager Jim Leyland.
Bobby Bonilla's time playing winter league baseball with the Mayagüez Indians in Puerto Rico came to an end after the 1988 season.
Bobby Bonilla's outstanding performance, including leading the league in extra base hits in 1990, placed him among the top contenders for the National League MVP award.
Bobby Bonilla, along with Barry Bonds and Andy Van Slyke, formed a formidable outfield trio that helped propel the Pittsburgh Pirates to National League East Division titles in 1990, 1991, and 1992.
In 1990, Bobby Bonilla led the league in extra base hits, showcasing his powerful hitting ability.
Bobby Bonilla became a free agent on October 28, 1991.
Bobby Bonilla signed a five-year, $29 million contract with the New York Mets on December 2, 1991, setting a record for the highest single-season salary in baseball history.
Bobby Bonilla signed a lucrative contract with the New York Mets during the 1991-1992 offseason, becoming the highest-paid player in the league.
Bobby Bonilla continued to excel offensively in 1991, leading the league in doubles.
In February 1992, Bobby Bonilla and his wife, Millie, established the Bobby and Millie Bonilla Public School Fund with an initial contribution of $35,000. The fund's purpose was to support schools attended by the couple.
Bobby Bonilla's record-breaking contract made him the highest-paid player in the National League from 1992 to 1994.
The Pittsburgh Pirates' streak of three consecutive National League East Division titles ended in 1992.
Bobby Bonilla achieved a career-high 34 home runs in 1993.
Bobby Bonilla's reign as the highest-paid player in the National League concluded in 1994.
On July 28, 1995, Bobby Bonilla was traded to the Baltimore Orioles.
Bobby Bonilla earned his final All-Star selection as a member of the New York Mets in 1995.
In 1995, Bobby Bonilla was traded to the Baltimore Orioles.
Bobby Bonilla played a significant role in the Baltimore Orioles' journey to the 1996 American League Championship Series.
After the 1996 season, Bobby Bonilla became a free agent and signed with the Florida Marlins, where he was reunited with his former manager, Jim Leyland.
As a member of the Baltimore Orioles, Bonilla contributed to the team's successful run to the American League Championship Series in 1996.
Bobby Bonilla was part of the Florida Marlins team that won the World Series in 1997.
In 1997, Bobby Bonilla won the World Series as a member of the Florida Marlins.
The year 1997 marked a resurgence for Bobby Bonilla, as he achieved his highest batting average since that season.
On May 14, 1998, the Florida Marlins traded Bobby Bonilla to the Los Angeles Dodgers as part of a multi-player deal.
The New York Mets reacquired Bobby Bonilla in a trade with the Los Angeles Dodgers in November 1998.
Bobby Bonilla had a short stint with the Florida Marlins in 1998, playing in only 18 games before being traded.
Bobby Bonilla was traded to the Los Angeles Dodgers midway through the 1998 season.
After his release from the Mets in 1999, Bobby Bonilla agreed to a deferred payment plan where he would receive annual payments of $1.19 million every July 1st from 2011 to 2035.
Bobby Bonilla rejoined the New York Mets in 1999.
Bobby Bonilla's second stint with the New York Mets in 1999 was marked by conflicts with manager Bobby Valentine over playing time and a controversial incident during the 1999 NLCS, ultimately leading to his release from the team.
In 2000, Bobby Bonilla signed with the Atlanta Braves, where he played 114 games.
On October 7, 2001, Bobby Bonilla played his last game in Major League Baseball. He retired at the end of the season, citing injuries and reduced playing time as the reasons.
After stints with the Atlanta Braves and St. Louis Cardinals, Bobby Bonilla retired from Major League Baseball at the end of the 2001 season.
Bobby Bonilla retired from Major League Baseball after the 2001 season.
Bobby Bonilla's deferred payment plan with the Baltimore Orioles commenced in 2004, paying him $500,000 annually.
Bobby Bonilla's deferred payment agreement with the Mets came under scrutiny in 2008 during the investigation of the Bernie Madoff Ponzi scheme.
In 2009, Bobby Bonilla and his wife Millie divorced after being married for over 20 years.
Bobby Bonilla's deferred payment plan with the Mets began in 2011, with him receiving $1.19 million every July 1st. This date has become known as "Bobby Bonilla Day" among Mets fans.
Bobby Bonilla's deferred payment plan with the Baltimore Orioles will conclude in 2028.
Bobby Bonilla's deferred payment plan with the Mets is set to end in 2035.