The Chicago White Sox are simultaneously one of the most historic and most inept franchises in MLB. While their origins stretch back to the 19th century and they have had some of the greatest players in baseball history make their name with them, they did go 88 years between championships in 1917 and 2005. That led to some really poor seasons, wherein these four White Sox only led the team in WAR due to the lack of quality talent around them.
4. 2B Cass Michaels (1949)
Oh dear, the post-WWII White Sox had some stinkers, and the 1949 team stands out as one of the worst in the history of the franchise. 5.3 wins above replacement was good enough to set the standard that year, and that's exactly what Michaels, a two-time All-Star second baseman, did, hitting .308 while driving in 83 runs. Michaels' pro career ended at the age of 28 in 1954, as a beanball that hit him in the head nearly killed him and significantly impaired his vision.
3. OF Ivan Calderon (1987)
The late-80s White Sox were fun to watch due to the colorful uniforms and personalities, but they didn't always provide South Siders with tons of success on the field. A 77-85 team in 1987 didn't have a ton of stars, but Calderon broke out, slamming 28 home runs and leading the team with 4.2 WAR. Calderon would never replicate his prodigious power, as he never topped 20 home runs again for the remainder of his career, though he was selected as an All-Star with the Montreal Expos
2. SS Ozzie Guillen (1988)
Popular as a player and successful as a manager, Guillen was not a good hitter, as he hit .261 with a whopping zero home runs and 39 RBI during the 1988 season. Still, somehow, Guillen and his nice 69 career OPS+ made three All-Star teams, one of them coming in a 1988 season in which he led the White Sox with 3.4 WAR. As evidenced by the fact he was their best player, Jim Fregosi's White Sox were putrid, winning just 71 games.
1. SP Esteban Loaiza (2003)
Before his second act as a cocaine baron, Loaiza was dominant for the 2003 White Sox. A journeyman up until that point, Loaiza won 21 games, posted a 2.90 ERA, compiled 7.2 wins above replacement, and emerged as the ace of a White Sox staff that helped Jerry Manuel guide this team to 86 wins. While Loaiza would have several successful seasons after this, including a brief stint with the Oakland Athletics after cashing in as a free agent, he was out of baseball by 2008, and his post-baseball life has cast a black cloud over his pro accomplishments.