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  • Gary Sheffield, an Immensely Talented, Polarizing Part of Brewers History

    Matt Breen

    There are many "what might have been" moments in the history of any franchise. The Brewers reportedly wanted to draft Mike Trout in 2009, but the Angels took him one slot ahead of Milwaukee. Or how about if Nomar Garciaparra had signed with the Brewers after he was selected in 1991 instead of choosing college? Another great ‘what if’ surrounds Gary Sheffield, who came up with Milwaukee with great fanfare in 1988 at the age of 19 - only to be traded after showing promise - but also inconsistency and immaturity. He went on to have a long and stellar career.

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    Gary Antonian Sheffield was born in Tampa Bay, Florida, in 1968. His uncle is Dwight Gooden - who was four years older. As a senior in high school, he was named the Gatorade National Player of the Year.

    The Brewers selected Sheffield in the 1st round of the 1986 draft - the sixth overall pick. It didn’t take long for Sheffield to become one of the top prospects in baseball. At Helena, Sheffield hit .365 and walloped 15 HR in just 57 games. He was only 17 years old.

    The abuse of minor league pitching continued as Sheffield showed an advanced hit tool, power, and a great eye at the plate. In 1988, at 19, Sheffield would debut in Milwaukee - playing 24 games. 

    However, there were signs of trouble ahead for Sheffield when he was arrested in early 1987 - alongside Dwight Gooden - and charged with resisting arrest and battery of an officer. Later that year, he was arrested for a DUI. 

    Besides a 7-game stint in the minors in 1989, Sheffield stayed in the big leagues. In his rookie campaign, Sheffield had mixed success as he battled several injuries - and a move to third base in favor of Bill Spiers. He hit only .247 in 94 games that year and said his move to third was race related.

    1990 demonstrated the enormous potential that Sheffield possessed. Working with hitting coach Don Baylor, Sheffield hit .294, although his considerable power had yet to emerge. But the fans and the Brewers thought they saw a star in the making.

    But there were cracks in the relationship between Sheffield and the organization and the fans. His willingness to candidly discuss racial issues was not common at the time, making many fans, members of the organization, and some of his teammates uneasy. Sheffield complained about the team favoring white players and how the organization mistreated him. He was generally portrayed as a talented but disloyal and immature malcontent. 

    Had Sheffield come into 1991 and hit well - all of these things would likely have been put aside - at least for a time. Instead, it would be a lost year. Various injuries would limit Sheffield to 50 games - and he hit a paltry .194. Fans booed Sheffield mercilessly, who later admitted he was miserable and requested a trade (something he had already done more than once). 

    Organizations are often hesitant to trade talented players - even if they are struggling - for fear they will find themselves in a new city. But the Brewers had had enough of Sheffield. On March 26, 1992, they pulled the trigger on a trade sending the talented but troubled infielder to the San Diego Padres for pitcher Ricky Bones, SS José Valentin, and OF Matt Mieske.

    Much to the Brewers' chagrin, Sheffield turned into an all-star in San Diego, hitting .330 and 30 home runs and winning the NL batting title. The Brewers won 92 games that year - but missed the playoffs. Had Sheffield been in the lineup, things may have turned out differently.

    We don’t need to go on about Sheffield’s career, but the numbers are quite astonishing. 509 HR. Almost 2700 hits. 9 All-Star teams. More walks than strikeouts. 

    Sheffield was not without his warts. He was never a good fielder. After leaving Milwaukee, he stayed at third base for a time before being moved to corner outfielder and finishing his career as a designated hitter. He never went back to shortstop, save for a few games here and there.

    He was also a baseball nomad - playing for eight teams in 22 years - often wearing out his welcome due to his quick temper, outspoken opinions, and a seemingly never-ending desire for a better contract. Sheffield’s supporters say he was simply an honest man - willing to talk about uncomfortable topics that many felt were too often swept under the rug. 

    Sheffield also had other issues - including multiple arrests for DUI, speeding, and altercations with fans. But the issue that - to this day - looms over Sheffield is regarding performance-enhancing drugs (PEDs). 

    Sheffield was mentioned in the Mitchell Report and implicated in the 2004 BALCO scandal concerning using PEDs. And he was named in the book Game of Shadows as having received testosterone and human growth hormone from Greg Anderson, the personal trainer he shared with Barry Bonds.

    Without those accusations, Sheffield may have reached the Hall of Fame. He received 40% of the vote in 2022 - but with only two more years of eligibility left in his candidacy - he’s unlikely to receive the 75% needed for induction.

    After baseball, Sheffield formed the Sheffield Management Group and became a sports agent.

    As we think about the ‘what ifs’ of baseball - it’s easy to look at 1992 and wonder if having Sheffield in the lineup would have helped the Brewers capture the NL East crown (the Brewers were four games behind Toronto). Kevin Seitzer had a solid season at 3B for the Crew that year, but it was nothing like Sheffield’s monster numbers.

    Yet even if Milwaukee had kept Sheffield, you have to wonder if he would have realized his full potential, especially considering the animosity between him and the organization. 

    Even if Sheffield had stayed in Milwaukee and played well, it’s unlikely he would have lasted with the Brewers. The team went into a long string of losing seasons starting in 1993, and Sheffield would have likely been traded at some point. His bat would not have elevated the team to playoff contenders during that time, making him more alluring as a trade candidate than a long-term fixture. The only good thing would have been the team could have netted a more substantial return than what they received from San Diego.

    Regarding the players brought in from San Diego, the results were uninspiring. Mieske was average in many ways. Ricky Bones wavered between ‘not bad,’ ‘bad,’ and ‘really bad'. Only SS José Valentin emerged as a solid, everyday player and would later be flipped for pitcher Jaime Navarro.

    The Brewer career of infielder Gary Sheffield was tumultuous. He was a talented young man, but the Brewers and Milwaukee were the wrong place for him to start his career. He was immature in many ways, and in an era of staying quiet and letting your bat do the talking, Sheffield was not embraced by the blue-collar - and mostly white - Brewer fan base. 

    Please share your memories about his short - but controversial time - in Milwaukee.


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    We don’t need to go on about Sheffield’s career, but the numbers are quite astonishing. 509 HR. Almost 2700 hits. 9 All-Star teams. More walks than strikeouts. 

    That is...surprising and incredibly impressive. 

    I didn't realize he was that disciplined of a hitter. Some of the quickest hands I've ever seen and the obvious comp when Rickie Weeks came along. 

    Seems to me like both sides handled this situation poorly...and the 20 year old phenom is generally going to be the one who ends up looking bad. 

    I know there were accusations of him faking an injury after playing poorly, then being sent down...playing poorly there and then him insisting his foot was in fact hurt, then later realizing they'd missed a fracture in his foot. 

    30 years ago now, so assigning blame is kinda pointless.With that said...I still harbor a great deal of resentment to Bando for ruining my childhood and forcing Molitor out of Milwaukee!

    I don't know if that should actually be in blue.

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    Loves sheff when he came up but he really didn't want to be in Milwaukee and that was pretty clear.. Quick hands and a very good hitter and his being close to Bonds and the steroid thing really hurt his career. Were Roids part of his greatness? That will always be part of the discussion won't it? Gary did have a very good career..

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    42 minutes ago, DougX57 said:

    Loves sheff when he came up but he really didn't want to be in Milwaukee and that was pretty clear.. Quick hands and a very good hitter and his being close to Bonds and the steroid thing really hurt his career. Were Roids part of his greatness? That will always be part of the discussion won't it? Gary did have a very good career..

    Welcome to the site!

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    Kevin Seitzer had a career year in 92 but Sheffield could have been the player that put them over the top and into the playoffs. If there is one move in Brewers history I could take back it would be this one because there has not been many years the Brewers could have won the World Series but 92 was one of them. 

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    I think Sheffield fits in well with the recent theme of general managers perhaps underestimating the ripple effect of their moves - e.g. Rodgers reacting to loss of Adams, Brewers' roster reacting to Hader trade, Sheffield reacting to trade of Dave Parker prior to 1991 season.

    I remember when a young Sheffield was upset that Bill Spiers played shortstop ahead of him, but in 1990 he nicely restored his full prospect value: 116 OPS+ in 547 PAs as a 21-year old. However, the team went 74-88 as they allowed the most runs in the American League and Molitor was limited to 103 games.

    With the club ready to move on from the 39-year old Parker (who was actually terrific in 1990, then struggled in 1991, essentially proving the Brewers' wisdom in trading him), this was actually the time (e.g. December 1990) to also trade Sheffield rather than risk him falling into a funk without his mentor Parker around.

    It's remarkable that the 1991 club was actually respectable, despite Sheffield doing nothing and the team's new spending (e.g. Franklin Stubbs, Edwin Nunez, raises for Ted Higuera and Chuck Crim) not panning out.

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