15 worst trades in Chicago White Sox franchise history

Cleveland Indians v Chicago White Sox
Cleveland Indians v Chicago White Sox / Ron Vesely/GettyImages
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No. 11: Danny Darwin, Wilson Álvarez and Roberto Hernández to the San Francisco Giants for Brian Manning, Lorenzo Barceló, Mike Caruso, Keith Foulke, Bob Howry and Ken Vining - July 1997

Infamously known as "The White Flag Trade", this blockbuster was negatively received by fans of the White Sox when it went down. The team was only 3 games out of first place, after all, so it's easy to understand why there's so much hate.

Going out the door was starting pitcher Danny Darwin, who had been worth 1.5 bWAR through the first 21 appearances of his White Sox tenure (at the age of 41 nonetheless!); Wilson Álvarez, who had been an above-average starter for the club the past seven years and Roberto Hernández, the club's closer.

This monster of a deal saw a massive chunk of the White Sox's pitching staff go out the door and a full-blown rebuild begin.

Starting off with the incoming player who contributed the least to the White Sox, outfielder Brian Manning never even made it to the big leagues with the club, retiring at the tail end of the 1999 season at 24 years old.

Barceló made 43 relief appearances for the club over the next three seasons, posting a combined 109 ERA+ along the way. He never amounted to much, but he was nine percent above league-average at that time.

Vining, a left-handed reliever, made eight appearances for the Sox in 2001, allowing 13 earned runs in 6.2 innings of work, walking seven, and striking out only three.

Caruso, a middle infielder, played 269 games for the Sox in two seasons but was one of the least productive batters of his time and was also an awful baserunner. He led the league in failed stolen base attempts with 14 in 1999.

What keeps this deal away from the top of this list is the acquisitions of Howry and Foulke. Both of these players were relief weapons for the White Sox. Howry stayed in Chicago for five years and had a combined 3.74 ERA and 127 ERA+ in 322 innings of work.

Foulke was even better, playing six years for the team and posting a 2.87 ERA and 166 ERA+ in 446 innings of work. Neither of them was around for much winning from the White Sox, but they both performed exceptionally well for the team during their time.