The South Siders swing a solid, three-player deal
1937
It was a deal met with outrage from Detroit fans, as the Tigers sent outfielder Gee Walker, catcher Mike Tresh and third baseman Marv Owen to the White Sox for starting pitcher Vern Kennedy, outfielder Dixie Walker and third baseman Tony Piet.
Dixie was still a promising youngster, but put up just 2.8 total WAR for the Tigers before being dealt to the Brooklyn Dodgers, where he would achieve his superstardom. Kennedy did get off to a 9-0 start in 1938, but leveled off and was traded to the Browns in early 1939. Piet was on his way out of baseball.
Gee had just come off of two straight 3.0 WAR-plus seasons with MVP consideration — part of the Detroit fan outrage — but leveled off in Chicago, with just 2.3 WAR in two White Sox seasons. Owen was on the wrong side of 30 and a non-factor. But Tresh was a prime prospect that made Tigers fans howl over losing. The backstop did have two standout seasons on the South Side to earn himself MVP votes, including a 2.1-WAR year in 1945; his value was more in bulk play, serving in Chicago for 11 seasons and 989 games but putting up just 2.2 career WAR.
Tigers fans were so angry, owner Walter Briggs had to issue an offseason statement claiming he signed off on the deal in an attempt to take the heat off of his front office.
All in all, though, the trade was a wash.
1948
The White Sox dealt Frank Papish to Cleveland for Bob Kuzava and Ernest Groth.
Kusava filled a swingman role for the 1949 White Sox fairly well, earning 1.4 WAR for a 10-6 record and 3.71 FIP/4.02 ERA/104 ERA+. He was dealt to Washington in May 1950 and had a phenomenal rest of season for the Senators before embarking on a mostly pedestrian remaining career; notable, that deal to Washington was the first of FIVE in-season trades Kuzava suffered in his career. Groth pitched in just three games for the 1949 White Sox and never saw the majors after that.
Papish would pitch in just 29 games over the next two seasons (0.4 WAR), making this trade a slight win for Chicago.
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 was made more expendable by the Dodgers having acquired Frank Robinson in a blockbuster deal earlier in the day.
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. Almost singlehandedly, Allen 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.
2010
After six seasons — a virtual lifetime in closer terms — the White Sox declined their option on Bobby Jenks, whose relationship with manager Ozzie Guillén had soured.
Jenks was plucked off of waivers by GM Ken Williams in December 2004, and by mid-September of the next year became the closer on an eventual World Series-winning club. He logged at least 27 saves in all five full seasons he pitched for the White Sox, and remains No. 2 overall in franchise annals with 173.
Jenks signed a two-year, $12 million deal with Boston three weeks after his Chicago release, but never saved a game for them, succumbing to a debilitating back injury and botched surgery.