For most of his career, Sheffield played right field, though he has also played left field, third base, shortstop, and a handful of games at first base. He played for the Milwaukee Brewers, San Diego Padres, Florida Marlins, Los Angeles Dodgers, Atlanta Braves, New York Yankees, Detroit Tigers, and the New York Mets. Sheffield was a first-round pick of the Brewers, who selected him sixth overall in the 1986 amateur draft after a standout prep career at Hillsborough High School in Tampa, Florida. He bats and throws right-handed.
Sheffield hit his 500th home run on April 17, 2009. As of his last game, Sheffield ranked second among all active players in walks (1,475), third in runs (1,636), fourth in RBIs (1,676), fifth in hits (2,689) and home runs (509), and sixth in hit by pitches (135).
Sheffield's batting swing was an exemplary mix of savage speed and pinpoint control. Despite his high home run total, Sheffield only topped 80 strikeouts twice in 22 seasons, while finishing his career among the all-time top 20 walks leaders. Because of his combination of skill, sportswriter Joe Posnanski wrote, "I can’t imagine there has ever been a scarier hitter to face." His first manager Tom Trebelhorn said, "Gary can turn on a 38-caliber bullet.”
He is the nephew of Dwight Gooden. After retirement, he started to work as an agent. His current clients include Texas Rangers reliever Jason Grilli.
Sheffield was born in Tampa, Florida, and grew up in Belmont Heights, near the Ponce de Leon projects. He and his family lived with his uncle, Dwight Gooden, who would go on to become the ace pitcher for the New York Mets. They played baseball frequently and Sheffield learned how to hit a fastball from Gooden, who is only four years older than he is. Sheffield has publicly said that his grandfather had a significant positive impact on his life, influencing him as a person and as an athlete.
Sheffield was a good hitter in the Little Leagues. However, Sheffield had problems with his temper and attitude, which would continue in the Major Leagues. Once, when he was late to practice, his coach benched him and Sheffield picked up a bat and chased the coach all over the field, resulting in him being kicked off the team for a year. When Sheffield was eleven, he was selected to the Belmont Heights Little League All-Stars, which included future Chicago Cubs #1 pick Ty Griffin, future Major Leaguer Derek Bell, and other future MLB players. The team made it to the Little League World Series finals, but lost to Taiwan 4–3. He set a record for doubles that would be broken in 2012 by Bradley Smith.
In 1983, Sheffield made the Hillsborough High School varsity baseball team. During his junior year, he bulked up to 175 pounds and was a pitcher and third baseman. During his senior year, his fastball reached the upper 80's and he frequently showed home run power. As a batter, Sheffield hit .500 and 15 home runs, in only 62 official at-bats. At the end of the season he was named the Gatorade National Player of the Year.
After high school, the Milwaukee Brewers drafted Sheffield with the sixth pick of the first round of the 1986 MLB draft. After being drafted he was shipped to Helena of the Pioneer League, where he had a .365 batting average and 71 RBIs in 57 games. The only question was what position he would play. He was slotted at shortstop, but struggled at the position, committing many errors and wild throws. In 1987, he was assigned to Stockton of the Class-A California League, where his defense improved and he produced at the plate. His batting average went below .300, but he led the league in RBIs with 103, and at the end of the year he was voted the Brewers' best prospect. In his third season, he went from Double-A to the majors. In 134 games for the El Paso Diablos and Denver, he batted .327 with 28 homers and 118 RBIs and was considered ready for the majors.
Sheffield was called up from the minors when rosters were expanded in September and made his major league debut on September 3, 1988. As a teenager, he got off to a fast start, with his first career hit being a home run off Mark Langston, though Sheffield finished the season with a .238 batting average and four home runs in 24 games. After a decline in play and several injuries, he found himself competing with Bill Spiers in a race for starting shortstop. After this, he was moved to third base and criticized the team, saying it was a black and white issue. At the end of the 1989 season, he batted .247 with five home runs and 32 RBIs. In 1990, he worked under Don Baylor, who had been hired as their hitting coach. He finished the season batting .294, with 10 home runs. While his playing improved, there were issues with Sheffield in the clubhouse, and went as far as accusing the organization of being racist after keeping him at third instead of playing him at shortstop where the white Spiers played. In his final season with the Brewers, he injured his wrist, thumb, and shoulder, playing in only 50 games.
After four seasons in Milwaukee, the Brewers traded Sheffield to the San Diego Padres for Ricky Bones, José Valentin, and Matt Mieske on March 26, 1992. Sheffield faced his uncle Dwight Gooden for the first time in a Major League game on May 12, 1992, getting a hit in three at-bats. In his first All-Star season, he contended for the Triple Crown for much of the year; while he missed out on the home run (33, two fewer than the leader, teammate Fred McGriff) and RBIs (100, nine fewer than leader Darren Daulton) titles, he won the National League batting title (the only one of the nine in Padre history not won by Tony Gwynn) with a .330 average.
In 1993, he started the season by hitting 10 home runs and batting .295 and was traded in midseason to the Florida Marlins.
On June 24, 1993, he was traded, with Rich Rodriguez, to the Florida Marlins for Trevor Hoffman, José Martínez and Andrés Berumen. He finished the season hitting 10 home runs, batting .292 and knocking in 37 runs while with the Marlins, and was the starting third baseman for the NL in the All-Star Game. At the end of the season, the Marlins gave him a four-year deal that made him the highest-paid player at third base. During the 1994 season, the Marlins moved him from third base to right field, where he showed great success with an impressive arm. Sheffield hit 112 home runs with the Marlins from 1994 to 1998, including 42 in 1996, making the All-Star Game in 1996, and leading them to victory in the 1997 World Series against the Cleveland Indians. He was traded to the Los Angeles Dodgers in 1998 because the Marlins allegedly could not afford a contract extension and because the Dodgers' parent company at the time, News Corporation, was looking to secure a television contract with the Marlins in exchange for trading popular Dodger Mike Piazza.
On May 14, 1998, he was traded along with Manuel Barrios, Charles Johnson, Bobby Bonilla, and Jim Eisenreich to the Los Angeles Dodgers for Mike Piazza and Todd Zeile. Sheffield finished the season with the Dodgers batting .316 and hitting 16 homers while driving in 57 runs. In 3½ seasons with the Dodgers, he hit 129 home runs and drove in 367 runs. He made three All-Star games while playing with the Dodgers and had become one of the best outfielders in the game. But during the offseason, he began lobbying for a trade because he thought the Dodgers were spending their money stupidly and sliding in the wrong direction, and publicly criticized coaches and teammates.
On January 15, 2002, Sheffield was traded to the Atlanta Braves for Brian Jordan, Odalis Pérez, and Andrew Brown. He spent two seasons with the Braves hitting 64 home runs and knocking in 216 RBIs including 132 in 2003. After two seasons with the Braves, he became a free agent for the first time in his long career on October 27, 2003.
On December 19, 2003, after negotiations between Sheffield and George Steinbrenner, a contract was agreed upon with the New York Yankees worth $39 million over three years. This deal included $13.5 million in deferred money and a $13 million team option for 2007. He joined a lineup that included Derek Jeter, Jason Giambi and the newly acquired Alex Rodriguez. In his first season with the Yankees, Sheffield started slowly, but finished the season with 36 home runs, 121 RBIs, and a .290 batting average, helping him finish second in the MVP voting behind Vladimir Guerrero. On July 27 Sheffield hit his 400th career homerun off of Micheal Nakamura of the Toronto Blue Jays in the top of the 9th inning. In his second season with the Yankees, he continued to play well, hitting another 34 home runs and driving in 123 runs. Sheffield started the 2006 season on pace for a .300 batting average and 30 homers, before he collided with Shea Hillenbrand of the Toronto Blue Jays on April 29, 2006. He tried to play despite the injury, but ultimately needed wrist surgery. Sheffield did not return until late September. He had lost his right field job to Bobby Abreu, whom the Yankees had acquired in a trade deadline transaction. This forced Sheffield to play first base for the first time in his MLB career. At the end of the 2006 season, the Yankees picked up Sheffield's 2007 option and traded him to the Detroit Tigers.
On November 10, 2006, he was traded to the Detroit Tigers for minor league pitchers Humberto Sánchez, Kevin Whelan, and Anthony Claggett. After the trade, Sheffield agreed to a two-year, $28 million extension. In his first season with the Tigers, he hit 25 home runs, with 75 RBIs, and a .265 batting average. Sheffield also hit his first triple since 2004 and stole 20 bases for the first time since 1990. He was also one of only six batters in the AL to have at least 20 home runs and 20 stolen bases, along with Alex Rodriguez, Grady Sizemore, Ian Kinsler, B.J. Upton and former teammate Curtis Granderson.
On September 8, 2008 in a game against Oakland, Sheffield hit the 250,000th regular season home run in Major League Baseball history according to Baseball-Reference.com. The home run was a grand slam off Gio González; Sheffield had hit baseball's 249,999th home run against Gonzalez in his previous at-bat. Sheffield ended the 2008 season with 499 career home runs.
On March 31, 2009, Sheffield was released by the Tigers despite being owed $14M. The Tigers said in a statement that they wanted to have more versatility with the DH position.
On April 3, Sheffield agreed to a deal with the New York Mets for the 2009 season, and he finalized the deal the following day. On April 17, Sheffield hit his 500th home run in a game against the Milwaukee Brewers, becoming the 25th player in MLB history to reach that milestone, the first player to achieve this as a pinch hitter, and the first to do so in a Mets uniform. Sheffield would also become the third player in Major League history to hit home runs before age 20 and after age 40, joining Ty Cobb and Rusty Staub. Alex Rodriguez became the fourth player to do so in 2015. Sheffield sat out a game in August when the Mets declined to offer him a contract extension.
Sheffield did not play in 2010. Though he initially suggested he wanted to sign with a team for the 2011 season, he announced his retirement at the beginning of 2011 spring training.Became only the second Padres hitter in franchise history to win a batting title joining Tony Gwynn
Los Angeles Dodgers career leader in on-base percentage (.424), slugging percentage (.573), OPS (.998) and at-bats per home run (14.5)
Holds Los Angeles Dodgers single-season record for at-bats per home run (11.7 in 2000)
His Tampa team finished second in the 1980 Little League World Series
Is the first player to represent five different teams in the All-Star Game.
Holds Florida Marlins franchise record for home runs in a season (42) in 1996
Tied Paul O'Neill as the oldest player to hit 20 home runs and steal 20 bases in a season, at age 38 (2007)
First player to hit at least 25 home runs for 6 different teams
25th player in MLB history to reach 500 home runs, and the first player to do so as a Met
Had 8 seasons with 30 or more home runs
One of 2 players in MLB history, along with Fred McGriff, to have 30 or more home runs in one season for 5 different teams (Los Angeles Dodgers [×3]; New York Yankees [×2]; Atlanta Braves [×1]; Florida Marlins [×1]; San Diego Padres [×1])
Led National League in batting average (.330) and total bases (323) in 1992
Led National League in on-base percentage (.465) and OPS (1.090) in 1996
In 1987, Sheffield and his uncle, MLB player Dwight Gooden, were arrested after fighting with police and resisting arrest in Tampa, Florida. He was verbal about his need for sufficient financial compensation and respect, demanding better pay when he was with the Dodgers, and refusing to play in the inaugural World Baseball Classic, saying "[his] season is when [he's] getting paid."
On April 14, 2005, a Red Sox fan leaned over the railing at Fenway Park and distracted Sheffield as he was going to field a ball hit by Jason Varitek. After Sheffield took a swing at him with his glove, he threw the ball back into the infield, and then got into a verbal altercation with him. Fan Interference was not called, resulting in a game tying RBI Triple for Varitek. The fan, a long-time season ticket holder, was not ejected from Fenway Park, but he donated his remaining 2005 season tickets to charity in an effort to avoid any controversy for the remainder of the season. Sheffield was fined for the incident. Charges were dismissed against both the fan and Sheffield.
In the June 2007 issue of GQ magazine, Sheffield (a Detroit Tiger at the time) was quoted saying that there are more Latin baseball players than African-American players because Latinos are easier to control. "What I said is that you're going to see more black faces, but there ain't no English going to be coming out. ... (It's about) being able to tell (Latin players) what to do — being able to control them.... Where I'm from, you can't control us." He continued "They have more to lose than we do. You can send them back across the island. You can't send us back. We're already here."
During an July 2007 interview with HBO's Real Sports, Sheffield said that Yankees manager Joe Torre treated black players differently from white players during his time there, citing himself, Kenny Lofton and Tony Womack as examples. Lofton later agreed with Sheffield's comments about being treated differently, but disagreed that race was the motivating factor. After it was pointed out that Derek Jeter is biracial, Sheffield responded that he wasn't "all the way black."
On September 19, 2008, Sheffield was hit by a pitch from Cleveland Indians pitcher Roberto Heredia Hernández (pitching under the name Fausto Carmona at that time) and walked to first base. When Hernández (Carmona) threw to first base, he and Sheffield exchanged words and Sheffield charged the mound, attempting to tackle Hernández but was caught in a headlock and punched a few times on the top of his head by the young pitcher, leading to a bench-clearing brawl. Hernández and Sheffield were both ejected, along with Indians catcher Víctor Martínez and Tigers second baseman Plácido Polanco. On September 22, the commissioner's office announced four suspensions resulting from the brawl: Hernández was suspended for six games, Sheffield received a four-game suspension, and Martinez and Indians infielder Asdrúbal Cabrera each received three-game suspensions. Sheffield made statements after the suspension that the involved players from the Indians would be "penalized" by him as well.
During a workout with Barry Bonds in 2001, a cream was applied to Sheffield's knee by a trainer to help heal ripped stitches from a knee surgery. Sheffield states in his book, Inside Power, that he had no knowledge of the cream containing steroids, and had no reason to assume so at the time. He goes on to say in his book that the cream did nothing to strengthen his knee, and also states that a look at his numbers shows no improvement after the incident.
On December 13, 2007, Sheffield was named in the Mitchell Report as one of the players who had obtained and used steroids.
He and his wife Deleon reside in Tampa, Florida. They have three sons. Sheffield has four other children from previous relationships. Deleon is a gospel recording artist and has sung the National Anthem at both the old Yankee Stadium and Dodger Stadium. In October 1995, Sheffield was shot in his left shoulder after an attempted robbery when he stopped his car at a traffic light.