1977
In the wake of free agent defections by Richie Zisk and Oscar Gamble but aspiring to a second year of Rent-a-Player success, the White Sox signed Ron Blomberg to a four-year, $600,000 contract — an absolutely insane commitment to a one-dimensional slugger who had played in just 35 games over the prior three seasons due to injury. The three-sport prep star was a first round choice of the Yankees in 1967 but never played in more than 107 games in a single season of his career — and remember, these were uncharacteristically mediocre Yankees teams at the time.
Blomberg, mostly DHing, hit a game-tying home run in the bottom of the ninth inning of a raucous home opener win over Boston, but played in just 60 more games for the horrible 1978 White Sox with five homers, 22 RBIs, a .652 OPS and 82 OPS+, and -0.1 WAR. Owner Bill Veeck only turned his sights on Blomberg after Gamble took a last-minute offer from the Padres after the Sox thought they had a deal to keep him on the South Side.
Blomberg retired after the season, at age 30, and remains one of the worst free-agent signings in White Sox history.
1992
The expansion draft to stock two new National League teams in 1993, the Colorado Rockies and Florida Marlins, was held.
For the first time in expansion draft history, this 1992 draft used teams from both leagues to stock one-league-only teams. So because this expansion draft featured players exposed by American League teams, too, the White Sox lost pitchers Greg Hibbard (No. 12 pick overall) and Robert Person (No. 47) to the Marlins.
Hibbard never actually pitched for Florida, however, as the Marlins made a draft-day deal to send him to the Cubs. The southpaw was already at the end of his short career; after getting off to a 6.2 WAR in his initial 1989 and 1990 seasons on the South Side, he basically was negative-WAR after that, and was done for good in 1994.
Person, acquired by the White Sox from the Mets as a minor-leaguer, had a season-plus of strong play in the Chicago system before being snatched away by the Marlins. He pitched in 142 games over nine seasons, with a peak of 6.3 WAR over three years as a regular rotation member of the Phillies from 1999 to 2001.
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