The Chicago White Sox are having one of the worst seasons in Major League Baseball history. They made some more unfortunate history on Sunday when they lost their 20th straight game. They are the first team since 1988 to reach 20 straight losses. The losing streak has brought the White Sox to a dismal 27-87 record and 36.5 games out of the playoffs. At the trade deadline, the White Sox kept stars Garrett Crochet and Luis Robert Jr but that has not helped this season.

The 20 straight losses date back to July 10, when they beat the Minnesota Twins. Ever since they have only scored 48 runs while allowing 134. One more loss would tie the American League record of 21 from the 1988 Baltimore Orioles. The AL/NL record is 23 from the 1961 Philadelphia Phillies and the overall record is the 1899 Louisville Colonels with a 26-game slide.

The Oakland Athletics are next on the White Sox schedule. The A's are in last place in the American League West but are 8-5 since the All-Star Break. The AL record would be broken on Tuesday night if the losing continues. The AL/NL record would go down on Friday in a home game against the Cubs. Game 27 would be their home game against the Yankees on Monday, August 12.

The White Sox sold many pieces at the trade deadline but kept Garrett Crochet and Luis Robert Jr. Recent reports have suggested that both players could be traded in the offseason, giving fans another reason to look forward to the end of the season.

Future of the White Sox

Chicago White Sox left fielder Andrew Benintendi (23) hits a two-run home run against the Minnesota Twins in the seventh inning at Target Field.
Bruce Kluckhohn-USA TODAY Sports

The White Sox will almost certainly trade both Crochet and Robert this offseason. Both of their values will be sky-high and the prospect pool will improve dramatically. Coming into the season, MLB.com ranked their pipeline the 17th best in baseball. After trades at the deadline, it has gotten better but they need to get into the upper echelon.

Crochet and Robert would be the top players traded at the deadline, barring something very unforeseen. A Crochet deal would provide a bigger return than the Corbin Burnes deal did for the Brewers in 2023. When Burnes was dealt, he had just one year left before unrestricted free agency. Crochet will have three years of team control remaining.

The Baltimore Orioles will be a candidate to pair Crochet with Burnes. They have the top prospect pipeline in baseball and can blow the White Sox away with an offer. The Dodgers, Yankees, and Red Sox can also offer hauls of prospects and MLB-ready players to pry Crochet away.

As for Robert, the Philadelphia Phillies are the absolute perfect fit. The Phillies need a center fielder to complete their All-Star-caliber lineup and have the pieces to acquire him. They made moves to push for a World Series this year but if it does not work, expect them to make a move in the offseason.

Any team who does not land Juan Soto in free agency could make the move for Robert. If he ends up with the Mets, the Yankees could trade one of their outfield prospects, Spencer Jones or Jasson Dominguez, to replace Soto's production.

White Sox fans don't have much to look forward to this season, but the offseason could bring in two massive hauls of prospects to set the team up for a bright future.