1960
White Sox owner Bill Veeck made up for some of his bum deals after the 1959 season by getting pitchers Juan Pizarro and Cal McLish from the Reds for infielder Gene Freese. Manager Al Lopez and pitching coach Ray Berres had their eyes on Pizarro for a few years, but Milwaukee refused to deal him to the Sox. Veeck craftily got his friend Bill DeWitt of Cincinnati to swing a deal with Milwaukee, then shipping Pizarro to the South Side.
Pizarro was an enigmatic, moody pitcher but when he got on the mound, he was all business. Possessor of a blazing fastball, the lefthander had four seasons of double-figure wins in Chicago, among them 16 in 1963 and 19 in 1964. He totaled 75 White Sox wins between 1961 and 1966, and was a two-time All-Star selection.
1967
It was one of the worst deals ever made by GM Ed Short, hastening the demise of the long-winning White Sox.
Short sent infielder and base-stealer Al Weis along with outfielder, base-stealer and home-run hitter Tommie Agee to the Mets in exchange for former NL batting champ Tommy Davis, pitcher Jack Fisher and catcher Buddy Booker. Two years later, the Mets won the World Series — thanks in large part to the play of Agee and Weis. None of the players the Sox got in return did much for them.
Deals along those lines sent the franchise into a tailspin, and by September 1970 Short was fired.
1993
White Sox GM Ron Schueler’s luck with taking chances on hurt or limited free agents continued, as he signed Julio Franco to a contract. Franco would have a tremendous 1994 season hitting behind Frank Thomas, with 20 home runs, 98 RBIs, eight stolen bases and a .319 batting average in his one year in Chicago.
Franco played in Japan the next year because the Sox refused to meet his asking price on a new deal.