The Chicago White Sox will be obvious sellers at the MLB trade deadline. However, their biggest trade assets come with a major caveat.
It’s going to be difficult dealing Andrew Benintendi with him set to earn at least $15 million through 2017. It’ll be easier trading Luis Robert Jr, who will be one of the most coveted players at the deadline. However, Robert has a pair of club options worth $20 million over the next two seasons. The outfielder is currently batting below the Mendoza line, making potential trade partners a bit squeamish.
But the White Sox have thought of a plan. With many of their prospects hitting the majors, Chicago is looking to continue enriching their farm system with talent. Which is why Chicago is willing to offer cash in any trades involving Benintendi or Robert, via Ken Rosenthal and Will Sammon of The Athletic.
“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. In both cases, according to sources briefed on the team’s plans, the White Sox are open to including cash in trades,” they wrote.
Chicago White Sox’s Andrew Benintendi, Luis Robert Jr trade plans

Despite his massive contract, Benintendi is hitting just .246 with seven home runs and 27 RBI. He had 20 home runs in 2024, but Benintendi is no longer the All-Star he was in 2022. Chicago will have a difficult time offloading his contract, even if they offer to cover a portion.
For all of Robert’s struggles, he is a former 30+ home run, Gold Glove outfielder. When on his game, Robert is a consistent 20/20 threat. He already has 21 stolen bases on the season. A season prior, the outfielder stole 23 bags while hitting 14 home runs. Robert’s 2023 season is what teams would be reaching for in a trade, as he was named an All-Star after hitting 38 home runs and stealing 20 bases.
Which his club options are pricey, it also gives an acquiring team some extra control. He wouldn’t just be a rental, and his new franchise has to hope a change of scenery would supercharge Robert. The White Sox could be willing to help out financial there as well, offering some form of compensation if the option years are picked up.
“The terms of Robert’s contract, which includes the balance of his $15 million salary this season, plus separate $20 million options for 2026 and ‘27, would complicate any negotiations,” Rosenthal and Sammon wrote. “An acquiring team might want to include contingencies under which the White Sox pay part of Robert’s salaries if they exercise his option years.”
Other White Sox trade options

While Robert will be the big fish, Chicago has a few more intriguing trade options at the deadline. Starting pitchers Adrian Houser and Aaron Civale, who are both free agents after the season, will be readily available.
“Neither is anything close to an ace,” they wrote. “Houser, though, has a 2.15 ERA in five starts. And the White Sox acquired Civale in part because they projected he would have more value at the deadline than the player they traded for him, first baseman/outfielder Andrew Vaughn.”
After struggling at Triple-A in the Texas Rangers organization, Houser received a major league opportunity with the White Sox. He has made the most of it, pitching to a 2.15 ERA and a 22/10 K/BB ratio over his first five starts with the team. He won’t yield a king’s ransom, but Chicago would rather get a future piece back then see him walk for nothing.
The Sox decided their Andrew Vaughn experiment was over and dealt him to the Milwaukee Brewers for Civale. The Brewers had recently demoted Civale to the bullpen, leading to a trade. The righty allowed two earned runs, both walking and striking out four over five innings in his Chicago debut. With seven years and 123 games of MLB experience under his belt, any team in need of a starter will consider Civale.
The White Sox will have a number of crucial decisions to make at the deadline. But the universal answer to all their questions is a brighter future on the South Side.
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