Little Looie is waived into retirement
1938
Monty Stratton, just 25 and coming off of an amazing 15-5, 2.30 ERA, 4.9 WAR season that included All-Star honors, tore his right biceps in an exhibition game against the Cubs. The injury was so bad, it was thought the righthander’s career might be finished.
The White Sox sent Stratton to a bone and muscle expert who predicted that despite the tear(s) that the hurler could be throwing again in two weeks. Stratton would not see action in the majors again until May 13, pitching a scoreless inning vs. Cleveland. After resting for 10 more days, Stratton was back, throwing a normal workload — i.e., 17 of his 22 starts for the season were complete games.
Stratton ended up with a 3.9 WAR for 1938, and superstardom was on the horizon. However, that November Stratton accidentally shot himself while hunting, had his leg amputated, and never pitched again in the majors.
1968
The White Sox sell slugger Rocky Colavito to the Dodgers. Colavito had been acquired from Cleveland for help in the 1967 pennant race, but finished his career-worst full season adding little to the thin South Side offense — an 85 OPS+ over 60 games.
Los Angeles would end up releasing him on July 11.
With 44.8 WAR over just 12 full seasons, Colavito was one of the most prodigious sluggers in baseball history, with season comps including Reggie Jackson, Boog Powell, José Canseco, Harmon Killebrew, Ralph Kiner and Roger Maris. Colavito’s career comp, with 93.5% similarity, is Frank Howard.
1974
Future Hall-of-Famer and White Sox legend Luis Aparicio is waived by the Boston Red Sox, effectively ending his career at 2,677 hits and 506 stolen bases. Aparicio was inducted into the Hall of Fame in 1984, and resides there in a White Sox cap. In fact, Boston had the distinction of having waived two Hall-of-Famers on the same day, as along with Luis Orlando Cepeda was cut loose; Baby Bull caught on with Kansas City for the 1974 season and was a White Sox hitting coach in 1980 before his enshrinement in Cooperstown in 1999.
1987
In what turned out to be an utter steal of a swap, GM Larry Himes sends starter Joe Cowley to Philadelphia for outfielder Gary Redus.
Cowley, who in 1986 had pitched one average season in the White Sox rotation — a season that included one of the sloppiest no-hitters in MLB history — went 0-4 for the Phillies in five games in 1987 and never play in the majors again.
Redus would put up 3.5 WAR for the White Sox over 207 games in 1987-88, stealing 78 bases in 91 attempts (85.7%).