1971
It was the trade that perhaps saved the franchise. White Sox player personnel director Roland Hemond sent pitcher Tommy John and infielder Steve Huntz to the Dodgers for slugger Dick Allen.
Allen, one of the most prolific talents in the game, marched to his own drummer and was deemed difficult to handle by other teams and managers. White Sox skipper Chuck Tanner, who knew the Allen family for years, showed the slugger his due respect and thus got the best out of him. Allen, singlehandedly, nearly led the team to the 1972 playoffs, winning the American League MVP. He’d win two home run titles in his three years on the South Side and be named to three All-Star teams. His popularity kept the turnstiles spinning, and kept the White Sox solvent.
An hour later, Hemond stole pitcher Stan Bahnsen from the Yankees for infielder Rich McKinney. Bahnsen would win 21 games in 1972.
2002
It was a deal that didn’t work too well for the White Sox, as GM Ken Williams traded closer Keith Foulke, catcher Mark Johnson, Joe Valentine and cash to the A’s for closer Billy Koch and two players to be named later. (On December 16, the trade was completed when Oakland sent reliever Neal Cotts and right fielder Daylan Holt to Chicago.)
Koch never found the success he had in either Toronto or Oakland, in part because of a rare illness. Cotts, at least, would have a spectacular season in 2005 helping the Sox win the World Series.
Foulke meanwhile, would saved 44 games in 2003 and made the All-Star team. Williams may have had his hands tied, by the fact that manager Jerry Manuel had lost confidence in Foulke and refused to pitch him in key situations in the back half of the 2002 season.