A Most Hated Man – Gary Sheffield as a Brewer

Brewers fans hate Gary Sheffield. In a game where there are few universally held opinions, this statement might as well be chiseled in stone. Ask any Brewers fan why and they will tick off the usual list of Sheffield’s capital offenses: he complained all the time (true), he accused the Brewers organization of being racist (true), he faked injuries (untrue), he called Milwaukee “Hell” (true), and he purposely made errors in the field (probably untrue). Sheffield was traded away from the Brewers 25 years ago this spring, but to any Crew fan who recognizes the name, the anger is still there. No man who has ever worn a Brewers jersey – perhaps no man who has ever as much played against the Brewers – draws the ire of the Milwaukee faithful as much as Gary Sheffield.

This hatred is, as sports fandom “hatred” goes, is not entirely unjustified. But something is lost when fans so wholeheartedly dismiss Sheffield. Just as any villain is vital to the story in which they appear, Sheffield is an important figure in Milwaukee Brewers history. Other players have whined and half-assed groundballs and quarreled with management and demanded trades before, yet Sheffield became the long-standing target for fans – the poster child for the modern, ill-tempered athlete of “nowadays.” The story of Gary Sheffield is more complicated than a mere catalogue of his wrongdoings. He was perhaps the greatest prospect in Brewers’ history, the would-be golden link between the glories of ’80s and the promise of the ’90s. But all that was lost before it even started.

As the 1986 MLB amateur draft approached, the Brewers felt they had little chance of getting Sheffield. He had just been named the Gatorade high school player of the year and was seen by some observers as the greatest high school baseball prospect ever. Coming up in the baseball-fertile but crime-ridden Belmont Heights neighborhood of Tampa, Florida, Sheffield spent much of his time with his mother’s little brother, a boy just four years older than himself named Dwight Gooden. Gooden was obsessed with baseball and, while Gary showed talent, it was Gooden who forced the necessary discipline for the game upon him. When Gooden was drafted sixth overall out of Hillsborough High School in 1982 and became a Major League star at 19, Sheffield saw what the game could do for a poor black kid from nowhere. Following in his uncle’s footsteps at Hillsborough, Sheffield set out to get his.

By the spring of 1986, with Gooden the reigning NL Cy Young Award winner, Sheffield was putting together one of the greatest amateur seasons ever. He batted .500 with 14 homers, 22 walks, and ZERO strikeouts in just 64 at bats. He also pitched 62 innings, striking out 85 and registering a 1.81 ERA. While he could have made his way as a pitcher, it was his bat that titillated Major League scouts. The Brewers saw a future Hall of Famer in his vicious swing, but figured there was no way he would still be around then their pick, sixth overall, came up. But on draft day, the first four teams up opted for college players and the fifth, the Atlanta Braves, went with high school pitcher Kent Mercker. Taking Sheffield next was one of the easiest decisions the team had ever made. Upon being informed that he was now property of the Brewers, Sheffield needed to told where they played. He had never heard of the team.

After a brief hold-out (Sheffield also had scholarship offers to Miami and Florida State), the Brewers gave Sheffield a $152,000 signing bonus and sent him to Helena, Montana to join the Rookie League Gold Sox. Helena was a world apart from Tampa. Sheffield was lonely and mostly kept to himself during his first professional season. He was only 17 years old. The press reported on the red Corvette he had bought himself with his bonus money, the gold grill he wore on his front teeth, inlaid with his initials, and the glittery jewelry he liked to wear. The stories were usually written with the mildly condescending kind of tone older white sportswriters often used when talking about the habits of young, black athletes. They didn’t write about his homesickness, or the two children he had with two different women back in Tampa, or the biological father he grew up without. That wasn’t so easily observed as he showed up at the ballpark each day.

Mostly they wrote about that marvelous swing. Sheffield had fallen to the Brewers because other teams had preferred more polished college players. But in Helena, not even old enough to vote, Sheffield annihilated Pioneer League pitchers. He batted .365, belted 15 homers, and walked more often than he struck out. He won the league’s MVP award and was named Baseball America’s short-season player of the year, all before turning 18 years old.

Sheffield went back to Tampa that fall. In December, he was driving his Corvette and Gooden was driving his Mercedes-Benz, returning home from a basketball game with friends, when police stopped both cars after they were seen weaving through traffic. After the cars were stopped, there was an altercation. Police said that Gooden resisted arrest and that Sheffield fought with officers. The men with the two ballplayers said that the cops struck first, handcuffed Gooden and beat him when he was on the ground. Sheffield claimed he was only trying to help his Uncle. He said that the police had used racial slurs. Sheffield pled no contest just to get the matter over with and was given probation and community service. A few months later, Gooden checked himself into rehab for a cocaine problem. As Sheffield started the 1987 season with class A Stockton, he was being subjected to regular drug tests by the Brewers, despite no indications that he was using.

In Stockton, he had a few run-ins with the club. He missed a team bus and was fined. He didn’t run a ground ball and was benched. But he kept hitting. By now, still just 18, he was Baseball America’s #1 overall prospect. He hit with power, stole 25 bases, and walked nearly twice as often as he struck out. He had a violent swing and upper deck power matched with the plate patience of Wade Boggs. He was still a project in the field, though. Playing his preferred position of shortstop, he made 39 errors in 1987, but showed a strong enough throwing arm to gain consideration as a third baseman or outfielder. Still, Sheffield bristled. He clashed with Dave Machemer, Stockton’s manager, and felt he should be playing at a higher level. He nearly quit the team after Machemer fined him for not wearing a collared shirt on the team bus, a rule Sheffield claimed was not uniformly enforced. Press reports fawned over Sheffield’s talent, but usually included mentions of worries about him getting lazy, his troubles with authority, and – even though he kept passing them – the drug tests.

Sheffield moved up to AA El Paso in 1988 and smashed 19 homers with a .314 batting average in just 77 games before being summoned to AAA Denver. In the thin, Rocky Mountain air, Sheffield continued his tear, posting a .344/.407/.561 slash line. Sheffield was on his way to being named the Sporting News’ Minor League Player of the year when, on September 2, 1988, Brewers shortstop Dale Sveum broke his leg in a collision with left fielder Darryl Hamilton. Still in the race for the AL East, the Brewers summoned Sheffield to the majors and installed him as the team’s starting shortstop. A week later, still without a big league hit (he was the youngest player to see action the Majors that season by a year), Sheffield came to bat against Mariners ace Mark Langston in the bottom of the sixth inning in a game the Brewers badly needed to win. The Mariners led 1-0 and Langston had yet to allow a hit. On a full count fastball, Sheffield rifled a homer to tie the game. Five innings later, also against Langston, he drilled a walk-off single to win it. The next great Brewer, the papers gushed, had arrived.

It’s more difficult to name the Brewers’ greatest prospect of all-time than it is to name their most hated player off all-time. But, all things considered, they are one in the same. Neither Yount nor Molitor spent enough time in the minors to truly preview their talents. Flame-out studs like Danny Thomas, David Green, and Dion James were all highly regarded, but had evident flaws. B. J. Surhoff, Ben Sheets, and Ryan Braun all exceptional minor league careers, but none of them – nor Rickie Weeks, Prince Fielder, nor the recently-arrived Orlando Arcia – drew the same kind of universal lust as Gary Sheffield. Never before and never since has the educated baseball consensus held that the Brewers had such a special rookie player on their roster. He was to be the next great Milwaukee Brewer. And it would all fall apart before he turned 21.

Check back next week for part two of this article.