Gary Sheffield was one of the most enigmatic players of 1990’s baseball.
Primarily a right fielder, Sheffield also played around the diamond at first base, third base, and shortstop.
Along with multiple positions, Sheffield also saw time on multiple teams, his longest stint being with the then-Florida Marlins.
Despite never sticking to one position or one team, Sheffield was one of the most dynamic and feared right-handed bats in baseball during his two-decade career in the big leagues.
Primarily a line drive hitter who hit the ball hard, sportswriter Joe Posnanski said:
“I can’t imagine there has ever been a scarier hitter to face.”
Gary Antonian Sheffield was born November 18, 1968 in Tampa, Florida.
He was raised by his mother Betty Jones and step-father Harold Jones.
When he was a boy, Sheffield and his family lived with his Uncle Dwight Gooden, who taught Sheffield how to hit a fastball.
Gooden would later become a dominant pitcher for the New York Mets in the 1980’s.
Sheffield was 11 years old when he discovered his biological father was not Harold Jones, and this discovery had a profound but negative impact on him.
He joined gangs near the housing project in which he lived, but stayed clear of too much trouble by playing baseball.
He would practice hitting and pitching with Gooden and practice with his step-father Harold with rocks and a broomstick.
Sheffield played little league baseball in his hometown and proved himself to be a capable player.
He excelled not only as a hitter but as a pitcher as well, thanks to his Uncle’s tutelage.
Sheffield showed attitude problems, however, and often lashed out or showed a temper at coaches and fellow teammates, resulting in him being once kicked off a team after an altercation with a coach.
His temper led him to multiple fights in school.
In 1980, Sheffield and his Belmont Heights Little League All-Star team made it to the Little League World Series finals, where they lost to 4-3 to Taiwan.
In 1982, Sheffield’s little league team won the 1982 title.
At Hillsborough High School, Sheffield played third base and pitched some.
As Sheffield entered his junior season, he began displaying serious home run power and touted a fastball in the upper 80’s.
Sheffield was named the Gatorade National Player of the Year in 1983, when he hit .500 and mashed 15 home runs.
As scouts drew more interested, Sheffield continued to play better and better.
Billy Reed, Sheffield’s high school coach described Sheffield:
“Huge thighs, blazing bat speed, cockiness, and a snapping temper.” Scout John Young said that Sheffield was “simply the best high school player in the country.”
Sheffield was named a high school All-American in 1986 and USA Today named him the top high school player in the nation, echoing Young’s comments.
Minor League Career
After a stellar high school career, Sheffield was drafted sixth overall by the Milwaukee Brewers in the 1986 amateur draft.
Sheffield quickly began moving up the ranks in the Brewers’ minor league system.
Switching to shortstop from his natural third base, Sheffield hit .365 in Helena, Montana in the Pioneer League and was soon promoted to Class A Stockton, where he continued to impress in the California League.
In 1988, Sheffield was moved to AA and showed great promise as a prospect by hitting .327 and clobbering 28 home runs during stints on AA El Paso and AAA Denver.
The move to shortstop was a struggle for Sheffield, and he was moved back to third base upon arrival in Denver due to consistent defensive issues.
Sheffield was soon considered the Brewers’ best prospect and Sheffield was named minor league coplayer of the year by Sporting News.
Major League Career
After an impressive but short stint in the minor leagues, Sheffield was called up by the Brewers on September 3rd of 1988 when he was just 19 years old.
He hit his first home run on September 9th against the Seattle Mariners.
His short time in the majors in 1988 was exciting but proved disappointing, as Sheffield hit just four home runs and batted .238.
Milwaukee Brewers (1988-1991)
Gary Sheffield pic.twitter.com/uSgY4jgkbD
— OldTimeHardball (@OleTimeHardball) January 22, 2022
At the beginning of the 1989 season, Sheffield found himself competing to the Brewers’ starting shortstop with Bill Spiers, but remained at third base.
Sheffield’s time with the Brewers was marked by controversy, injury, and underperformance.
When the team moved him to third base instead of starting him at shortstop, he accused team management of being racist and began causing issues in the Milwaukee clubhouse.
The 1989 season saw Sheffield hit just .247 with five home runs and 1990 saw him hit .294 with 10 home runs.
While the 1990 season was an improvement over 1989, Sheffield continued to feud with Milwaukee’s front office.
In his final season in a Brewers uniform in 1991, Sheffield played in just 50 games after sustaining injuries to his wrist, shoulder, and thumb.
Unimpressed with his productivity and soured on his personality, the Brewers traded Sheffield to the San Diego Padres before the 1992 season began.
Sheffield exploded with the change of scenery, and made his first all-star team and nearly won the National League Triple Crown.
He finished 1992 with 33 home runs, 100 RBI, and won the N.L. batting title with a .330 average.
Sheffield also got the opportunity to face his uncle Dwight Gooden, getting one hit.
He began the 1993 season with the Padres but was unexpectedly traded to the expansion Florida Marlins after a firesale.
With the Padres, he hit .295 with 10 home runs before the trade.
1993 saw Sheffield make another all-star team, this time in a Marlins uniform.
He added 10 home runs as a Marlin and drove in an additional 37 runs.
The Marlins signed Sheffield to a four-year contract following the 1993 season and was soon moved from third base to right field.
As a Marlin, Sheffield proved to be one of the most productive and versatile players in the National League, hitting over 100 home runs between 1994 and 1998.
In 1996 he would make the all-star team and in1997, he helped lead the Marlins to a wildcard berth and their first World Series title in their short history over the Cleveland Indians.
After a career beginning in controversy and underperformance, Sheffield had transformed himself into a complete player with a World Series win under his belt.
In May of 1998, Sheffield was traded again to the Los Angeles Dodgers with others for slugging catcher Mike Piazza.
The Marlins figured they would not be able to extend Sheffield and wanted Piazza on the team.
In Dodger blue, Sheffield was again a productive player who hit for a high average and rarely struck out.
His swing was rocket fast and he became known primarily as a hard-hitting line drive hitter as opposed to a towering home run hitter and perhaps put up his best numbers for the Dodgers.
He finished his first all-star season in Los Angeles in 1998 batting over .300 with 16 home runs and finished in the league top 10 in on-base percentage, walks, and OPS+.
1999 and 2000 were some of Sheffield’s best career years.
In 1999, he slugged 34 home runs and drove in over 100 runs.
He finished in the top 10 once again in walks and on-base percentage, and made his second consecutive all-star game.
Sheffield’s eye was improving, and he began drawing more walks than strikeouts, only adding to his hitting prowess when combined with his lightning-fast bat speed and eye.
In 2000, Sheffield made another all-star team, a regular occurrence for Sheffield in L.A.
He finished the season with a career-high 43 home runs and batted .368 and placed ninth in the MVP vote.
In his last season with the Dodgers in 2001, Sheffield began once again to criticize team management and their decisions.
Despite the controversy, Sheffield finished the season as one of the premier outfielders in baseball, hitting over 30 home runs and again finishing in the top 10 for walks and on-base percentage.
Following the season, Sheffield requested a trade as he felt the team was moving in the wrong direction.
The Dodgers then traded Sheffield to the Atlanta Braves.
Sheffield spent only two seasons with the Braves.
Those two seasons proved that Sheffield was still on top of his game and one of the best hitters in baseball, however.
Now in his early 30’s, Sheffield hit over .300.
He made another all-star team in 2003, and finished his short stint in Atlanta by totaling 64 home runs and over 200 RBIs.
After the 2003 season, Sheffield became a free agent for the first time in his career, which was over a decade long at that point.
Sheffield signed with the New York Yankees, a three-year, $39 million contract.
Sheffield joined the powerhouse team led by Alex Rodriguez and Derek Jeter, looking to avenge their 2003 World Series loss to the Marlins.
Bobby Cox, Sheffield’s manager in Atlanta, said of Sheffield
“Gary, for two years, was pleasant. He’s a manager’s player. He was terrific. He came to play. Joe Torre will like him a lot.”
Sheffield continued to prove his worth in the Bronx, as he finished his first season finishing second in MVP voting with 36 home runs and over 100 runs driven in.
He also hit .290 and added veteran leadership to the clubhouse.
In his second season as a Yankee in 2005, Sheffield essentially replicated his 2004 numbers and solidified himself in the Yankees already-dominant lineup.
Off to a fast start in 2006, Sheffield lost his starting role to injury after an April collision with Blue Jays player Shea Hillenbrand.
After acquiring right fielder Bobby Abreu from the Philadelphia Phillies at the trade deadline, Sheffield shifted to first base for the first time in his career upon returning from his injury.
In his time with the Yankees, Sheffield made an additional two all-star teams (2004, 2005) and was one of the best hitters in the A.L. The Yankees traded Sheffield to the Detroit Tigers before the 2007 campaign.
In Detroit, Sheffield showcased his base-stealing abilities, one of six A.L. players with at least 20 home runs and 20 stolen bases.
He hit 25 home runs on the year and played a combination of the outfield and designated hitter.
He finished the 2008 season, his second in Detroit, with 499 career home runs.
Despite being a productive hitter with the Tigers, they released him before the 2009 season despite still owing him money from the two-year, $25 million contract they signed him to upon arriving in Detroit from New York.
As the 2000’s marched forward to the 2010’s and Sheffield turned 40, he joined the New York Mets in his final major league stop.
With the Mets, Sheffield hit his 500th career home run against the team that drafted and shipped him off, the Milwaukee Brewers.
Sheffield also became just the third player in history to hit a home run as a teenager and a home run in their 40’s, a club only inhabited by Ty Cobb and Rusty Staub.
After not being offered an extension by the Mets, Sheffield retired following the 2010 season, a season in which he did not play.
Despite Sheffield’s offensive numbers, he was often dragged down as a player by his lackluster defense around the diamond.
As the baseball world has moved toward using advanced metrics to properly evaluate players, defensive stats like UZR and DRS come more into play.
Both metrics show Sheffield’s defense as some of the worst in measured baseball history.
Sheffield may have lost close to 30 wins above replacement due to his dreadful defensive career.
Sheffield’s defense is the difference between him having 77 WAR and 62 WAR (wins above replacement), which would bring him into the top 50 of all time.
Life After Baseball
Sheffield finished his career as one of the best all-around hitters of the 1990’s and 2000’s.
He was selected to nine all-star teams, collected over 2,500 hits, has a career batting average of .292, and slugged over 500 home runs, and won a batting title.
He also finished in the top three in the MVP vote twice, won a World Series with the Florida Marlins, and won five Silver Slugger Awards.
Sheffield has been up for election into the Hall of Fame since 2015, but has yet to reach the 70% needed for induction.
Many speculate that Sheffield’s lack of significant time on one team, his controversial playing career, and his steroid connections are the main hindrances for his induction.
Like many superstar sluggers in the 1990’s and early 2000’s, Sheffield’s has been mentioned as a possible steroid user.
While training in the offseason with Barry Bonds, Sheffield recalled Bonds telling him:
“I got guys here, they can get your urine and blood and prescribe a vitamin specifically for your blood type and what your body needs.”
Bonds also introduced Sheffield to his weight trainer and the founder of BALCO, Victor Conte.
Both men would be indicted in 2004 on providing illegal steroids to professional athletes.
While being named in the Mitchell Report in 2007 as someone likely to have obtained and possessed steroids, Sheffield has denied any steroid use.
In his post-baseball life, Sheffield has joined broadcast booths to cover and analyze MLB games.
He also founded his company Sheffield Management and Entertainment, which serves as an agency for professional athletes and other entertainers.
Sheffield has also been vocal about race issues throughout his playing career and post-playing career.
In 2020, Sheffield wrote a piece for The Player’s Tribune following the death of George Floyd and the Black Lives Matter protests that followed.
In the piece, titled “Do You Believe Me Now”, Sheffield details his own experiences with police brutality, specifically an incident in 1987 in which he and Dwight Gooden were pulled over without cause and then beat them.
Sheffield said the police “beat all of us unmercifully” with flashlights, then took them to a dog track where they “proceeded to assault us again until we were black, blue, and swollen.”
In 2015, Sheffield and his two friends were pulled over by a policeman, which was followed by a K-9 unit and more police, where they began to search the car and throw its contents into the road.
When an officer told Sheffield to stop recording the incident and grabbed his arm, Sheffield told him to let go, which he did.
Sheffield points out that the:
“Unfortunate reality is that my stories aren’t unique. They’re not special or extraordinary, and neither am I. What happened to George Floyd could have easily, and far too often, happened to me or others.”
Gary Sheffield entered the 1990’s as a young firebrand talent with a knack for knocking the cover off a baseball.
He channeled his emotions and passions and frustrations into his play and soon became one of the most feared and dominant right handed sluggers in baseball for two decades.
An odd and interesting career, Sheffield remains one of baseball’s most enigmatic players and personalities.
He remains a role model for young players throughout the country due to his stellar career and vocal stance on issues of race and sports.
— Jay Recher (@jayRecher) January 22, 2022
Whether or not Sheffield finally gains entrance into the Hall of Fame, he will be remembered as an integral piece of the puzzle that is Major League Baseball in the 1990’s and 2000’s.