The Brewers drafted Gary Sheffield out of high school with the 6th pick of the 1986 draft. He came up through the minor league system in just three years and then played three years in the majors before he was traded to the Padres.
He started his minor league career on fire with the Helena Brewers batting .365 and 71 RBI in 57 games. He was named the Pioneer League's Player of the Year award and Baseball America's Short-Season Player of the Year award.
In his second year his batting average dropped, but he put up 103 RBI and was named the top prospect in the organization as well as making the California League and Baseball America All-Star teams. The Brewers drafted him as a short-stop and he had a hard time with the defensive aspects of this position, a problem that would dog him throughout his time with the Brewers.
In 1988, he started the season with in AA El Paso and made it to the majors as a September call-up at the age of 18. His first major league hit was a home run, but his offense didn't stand up to that beginning. He hit just .238 with four home runs in 24 games that first season.
He was brought in to the majors as an outfielder and third baseman. He was moved to short-stop after Dale Sveum got injured, but once again struggled defensively. He was sent down to the minors in July of 1989 for "indifferent fielding." Sheffield claimed an injured foot, but the club seemed to not believe him. Once he was in the minors, it was revealed that he had a fracture. "He didn't trust anyone after that," says Tom Trebelhorn, the Brewer manager at the time.
When he returned to Milwaukee, he was moved to third base, a move that led to malcontent and complaints from Sheffield. He claimed the choice to play him at third was racially motivated. From there, Sheffield's frustrations with the team seemed to follow him to the plate. "When a reporter wondered whether I thought the decision had racial overtones, I wasn't about to lie," Sheffield writes."
From his book "Inside Power"
"I've never been more miserable," Sheffield writes, referring to the time after the '91 season, when he played in only 50 games because of wrist and shoulder injuries. He batted .194, a career low.
"Milwaukee wasn't my kind of town. Milwaukee wasn't my kind of team. Far as I was concerned, Milwaukee was hell."
To top off the discontent, Sheffield claimed that then-owner Bud Selig offered him a long-term deal (stories vary on when the deal was offered) and then reneged.
Sheffield was so upset that he later said he purposely botched plays: As Sheffield said in the Los Angeles Times in 1992: "The Brewers brought out the hate in me. I was a crazy man … I hated everything about the place. If the official scorer gave me an error, I didn't think was an error, I'd say, 'OK, here's a real error,' and I'd throw the next ball into the stands on purpose."
Looking at his stats does not seem to back up his claim. He had just four multi-error games and none can be pinned down as purposeful.
He recanted the statement, also in the LA Times, "Sheffield said Monday: 'What I said was out of frustration. They want to take something and run with it. Why would a player purposely make mistakes? I'd never do anything to hurt the team. You get paid to play.' Sheffield said the only time he may have made an error purposely out of anger was when he was in the Brewer minor-league system."
With so much bad blood between player and club, it was inevitable that the Brewers would trade Sheffield. To add fuel to many Brewers fans hatred, when Sheffield got to the Padres, his stats improved immensely and he was a triple crown candidate.
For many, the final nail in Sheffield's coffin was his naming in the Mitchell Report. He testified that he'd never used strength-building steroids and has also said that he had used a cream on his knee, but didn't know that it contained steroids.
Despite living the life a journeyman, playing for eight different major-league teams, he was a nine-time All-Star, a five-time Silver Slugger and he became just the 25th person ever to hit 500 home runs. There is a legitimate case that can be made for his Hall of Fame candidacy.