Four trades, including two steals
1959
In an effort to ensure the White Sox would repeat as American League champs, Bill Veeck and Hank Greenberg decided to make a series of moves to bring in hitters — at the expense of some of the top young players in the Sox system.
Veeck originally tried to get young stars — like future White Sox coach Orlando Cepeda from the Giants and Bill White from the Cardinals — but was turned down. So, he went in the only direction he felt he could.
The first deal brought the Sox back outfielder Minnie Miñoso at the cost of two future All-Stars, first baseman Norm Cash and catcher Johnny Romano. Cleveland also got Bubba Phillips. White Sox manager Al Lopez was quoted after the controversial deal as saying, “Some of us, like me, are not worried about next year [1961] because we might not be around then.”
Cash and Romano alone would combine for 506 home runs and six All-Star appearances in their careers.
Miñoso would have an excellent season in 1960, hitting .311 with 20 home runs and 105 RBIs to go along with 17 stolen bases, making the All-Star team.
1984
It was one of the most brilliant and gutsy deals ever completed by GM Roland Hemond, one that paid dividends immediately — and 20 years down the line.
Hemond sent former Cy Young winner LaMarr Hoyt to the Padres in a package deal that netted the White Sox a 20-year-old shortstop named Ozzie Guillén. The Sox also got valuable utility player Luis Salazar and two pitchers, Tim Lollar and Bill Long.
Guillén immediately filled a gaping hole in the infield and was named Rookie of the Year in 1985. He’d win a Gold Glove and become a three-time All-Star in his White Sox career, before returning to Chicago as manager in 2004. He won the World Series in 2005 and made the playoffs again in 2008.
Hoyt was out of baseball by 1987, battling weight issues and drug addiction.
2002
Ken Griffey Jr. to the White Sox?
Yes, the White Sox would acquire The Kid six years later, but it was on this day that the Cincinnati Reds rang up GM Ken Williams and offered the superstar center fielder for Magglio Ordoñez. The White Sox, with Ordoñez in his prime and still two seasons away from any significant injury, refused.
The offer should not have been able to be made, as a week earlier Griffey was traded from the Reds to San Diego for Phil Nevin. However, Nevin exercised his no-trade clause and nixed the swap.
Although the White Sox would have Ordoñez for just two more seasons before he departed to Detroit via free agency, Chicago’s hesitance on this trade proved apt. Griffey played just 136 games in 2004 and 2005, struggling to just 1.9 WAR. Meanwhile Ordoñez managed 212 games and 6.4 WAR over the same time span.
Ordoñez was also much better in the long term, putting up 20.0 WAR to just 6.4 for Griffey in his career after 2002, despite playing just one more season and 249 additional games.
2005
Frank Thomas, the best hitter in team history but coming off of back-to-back injury-plagued seasons, became a free agent after the White Sox declined to pick up his $10 million option. GM Ken Williams had little choice in the matter after adding slugger Jim Thome in trade. At his age and weight, there was no longer a place for Thomas in the lineup.
The Big Hurt eventually signed an incentive-laden deal with the A’s in late January and continued his Hall of Fame career.
2006
GM Ken Williams pulled off a heist, sending starting pitcher and 2005 playoffs hero Freddy García to Philadelphia for starter Gavin Floyd and prospect Gio González (who had been dealt from the White Sox to the Phillies almost exactly a year earlier).
By 2008 Gavin had blossomed into a minor star and rotation stalwart, running up 16.5 WAR over five full seasons in Chicago. García faltered badly in Philadelphia and endured injured seasons with the Phillies and Tigers before kick-starting the final leg of his career back on the South Side, in 2010.
Gio, a future 28.3 WAR pitcher and two-time All-Star, would be dealt from the White Sox a little more than a year later in a package for Nick Swisher — one of the worst deals in franchise history.
2016
It was one of the biggest Winter Meetings trades in memory, as the White Sox sent Chris Sale, one of the top pitchers in the game, to the Red Sox for two plum prospects: No. 1-ranked minor league player in the game Yoán Moncada, and top pitching prospect Michael Kopech.
Sale was brilliant in his six-plus years with the White Sox, winning 74 games with a 3.00 ERA. He made the All-Star team five times, pitching five innings total and winning the 2013 contest. He set White Sox records for most strikeouts in a season (274) and had four consecutive years with more than 200. After four straight losing seasons, the White Sox decided it was time to rebuild, and Sale was in demand — so the painful decision was made to trade him and hope for a better future.