It was one of the worst deals in White Sox GM Ron Schueler’s career, as he traded pitcher Melido Perez and minor hurlers Bob Wickman and Domingo Jean to the Yankees for Steve Sax. Schueler envisioned a devastating 1-2 punch at the top of the order in Tim Raines and Sax, followed by Frank Thomas and Robin Ventura. It never happened, as Sax suddenly forget how to hit and was gone from the team by late April 1994. Making matters worse is that Wickman would go on to become a top relief pitcher and two-time All-Star, winning 63 games and saving 267 in his MLB career.
Sax did have one moment of glory with the White Sox. On May 5, 1993 in Milwaukee he made an incredible catch in left field on a ball hit by Bill Doran with the lead run on base. It happened in the eighth inning, when Sax broke back and to his left on the drive and caught the ball with his right arm extended. The angle and momentum caused him to tumble, and he lost the ball out of his glove on the way down. Just before hitting the ground, he snagged the ball with his bare left hand, holding it up to the umpire after he hit the grass. That saved a run, and the Sox won the game, 3-1, on a Ventura home run in the top of the ninth inning.
As the next step in their ill-fated “Manny Machado Friends and Family” caper to cajole the prime free agent target to Chicago, the White Sox signed journeyman outfielder Jon Jay to a $4 million deal. Jay was a close Machado friend, who along with Machado and Machado’s brother-in-law, Yonder Alonzo, fashioned the so-called Miami Baseball Brotherhood, training together in the offseason.
Despite immediate, embarrassing spins like Machado or no Machado, Jon Jay Brings plenty to White Sox, there was nothing about Jay’s mediocre career, or -0.3 WAR and 68 OPS+ in 2018 with the Diamondbacks, that warranted $4 million — beyond being Manny’s caddy.
The experiment was a disaster, as Machado spurned the White Sox for San Diego (with Jay and Alonzo rubbing in salt by praising their friend’s decision!) and Jay played just 47 games in Chicago, somehow surpassing his awful 2018 with -0.7 WAR as a White Sox.