The Chicago White Sox enter Friday's action with the worst record in the American League. That is far from surprising, as they had the worst record in modern MLB history last season. When the trade deadline came around in 2024, they sold off a lot of their pieces, including Erick Fedde and Tommy Pham. This year, the White Sox enter the MLB trade deadline with Luis Robert Jr and Andrew Benintendi as candidates. But Ken Rosenthal reported that the team knows they are going to have to retain salary to make those deals happen.

“The Chicago White Sox recognize they are in no position to impose the same conditions on teams that express interest in their two most expensive players, outfielders Andrew Benintendi and Luis Robert Jr,” Rosenthal wrote about the Red Sox mandating the Giants take all of Rafael Devers' contract. “In both cases, according to sources briefed on the team’s plans, the White Sox are open to including cash in trades.”

Benintendi has been miserable since signing the biggest contract in White Sox history. In 334 games, he has a 0.1 bWAR, 32 home runs, and 136 RBIs. His OPS is just .693, compared to a .782 mark for the first seven years of his career. The White Sox owe him $17 million this year and next year, and $15 million in 2027.

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Robert has independent team options in 2026 and 2027, so he could hit free agency as soon as this year. But another dreadful season does not mean great things for Robert's trade candidacy. The White Sox's centerfielder has a .576 OPS this year, but has already stolen 22 bases this year.

The White Sox traded Garrett Crochet in the offseason for four of the Red Sox's best prospects. If they can pick up a few more at the MLB trade deadline, the Southside could be set up for a successful rebuild after some dreadful seasons.