December 15, 1960 - Sox owner Bill Veeck made up for some of his 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 therefore got his friend Bill DeWitt of Cincinnati to swing a deal and then to ship 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 left hander had four seasons of double figure wins with 16 in 1963 and 19 in 1964. He was a two time All Star selection.
Sox catcher J.C. Martin remembered Juan when I asked him about him.
"Juan was pitching with Milwaukee and wasn’t doing very well. He was pretty wild but somehow Al Lopez and pitching coach Ray Berres saw something in him and we got him in a trade. Those guys knew more about pitching then anybody I’ve ever seen. They straightened him out. He was tough. He threw a wicked curve, a hard fastball and a good change."
December 15, 1967 – It was one of the worst deals ever made by then GM Ed Short.
The Sox sent infielder and base stealer Al Weis along with outfielder, base stealer and home run hitter Tommy Agee to the Mets in exchange for former N.L. batting champ Tommy Davis, pitcher Jack Fisher and catcher Buddy Booker. Two years later the Mets would win the World Series thanks in large part to the play of Ageeand Weis. None the players the Sox got in return did much for them. It was deals along those lines that sent the franchise into a tailspin and by September 1970 got Short fired from his position.
December 15, 1993 - Sox GM Ron Schueler’s luck with taking chances on hurt or limited free agents continued when he signed Julio Franco to a contract. Franco would have a tremendous 1994 season hitting behind Frank Thomas. Julio would have 20 home runs, 98 RBIs, eight stolen bases and a .319 batting average in his one year in Chicago. He went to Japan the next year because the Sox refused to meet his asking price on a new deal.