When the Brewers selected shortstop Gary Sheffield with the sixth overall pick in the first round in 1986, they thought they were getting a player with a bright big league career in front of him. They were right of course, but it wasn’t until after he departed Milwaukee that Sheffield’s Major League career really took off.
Sheffield started his pro career in the Pioneer League with Helena where he went on to destroy opposing pitching as the Brewers 17-year-old phenom went on to hit .365 with 15 home runs and 71 runs batted in in 57 games.
He was so dominant in his first season that Milwaukee saw fit to skip Sheffield over Low-A Beloit in 1987, sending him directly to High-A Stockton in the California League and hastening his path towards the big leagues. He held his own there in 129 games, batting .277 with 17 home runs and knocking in 103 runs for the Ports.
He split the following year between Double-A El Paso and Triple-A Denver, hitting a combined .327 with 28 doubles, 8 triples and 28 home runs, earning him a September call-up and at just nineteen years of age, Sheffield made his major league debut with the Brewers in a September 3rd contest in Detroit against the Tigers.
Sheffield spent the following three seasons with Milwaukee, with his best year coming in 1990, when he hit .294 with 30 doubles and 10 home runs in 125 games, but his time with the Brewers was marred by injuries, ineffectiveness and a public spat with the club that centered around a move from shortstop to third base. Unable to appease their young slugger, the Brewers traded Sheffield to San Diego in March of 1992 in exchange for pitcher Ricky Bones, outfielder Matt Mieske and infielder Jose Valentin.
The trade from Milwaukee seemingly re-ignited Sheffield, who went on to hit a league leading .330 in 1992 with the Padres, belting 33 home runs and knocking in 100 while being named to his first All-Star team that same season. His time in San Diego wouldn’t last long however, as Sheffield was dealt to the Florida Marlins the following June. He earned another All-Star nod with the Marlins in 1996 and helped lead the team to their first World Series title in 1997, before being traded once again in 1998, this time to the Los Angeles Dodgers in a blockbuster deal for Mike Piazza.
After his time with Los Angeles ended, Sheffield enjoyed stints with the Braves, Yankees, Tigers and Mets before retiring at age 40 following the 2009 season. Over the course of his 22-year Major League career, Sheffield hit .292 with 509 home runs, winning a World Series ring, five Silver Slugger Awards and finishing in the top ten for Most Valuable Player balloting six times.