Monday marked five days since the end of the World Series, meaning the official start of the MLB offseason. By the end of the day, MLB teams and players decided on club/player options and qualifying offers, and all 60-day IL players were activated to drop each team’s roster to 40. Free agent and trade activity is expected to pick up over the next few weeks ahead of the lockout, and another important deadline is quickly approaching on November 17th. By then, teams will have to decide whether or not to tender a contract for their arbitration-eligible players.
There’s an inevitable run of roster shuffling ahead of the deadline– one that included the White Sox acquiring Chris Murphy, Everson Pereira, and Tanner Murray in trades last season– and they could be looking for similar moves this year. Here are two players the White Sox could trade ahead of the non-tender deadline and what they might receive in return.
OF Andrew Benintendi
The owner of the largest contract in White Sox history, Andrew Benintendi has been little more than an average hitter during his four years in Chicago. He’s provided very little value on defense to go along with his inconsistent bat, so it’s hard to say his five-year/$75 million contract was worth it for Chicago. He has one year remaining on his deal, and this could be the ideal time for the White Sox to look for a trade and open up the DH role. Benintendi is owed $15.1 million in 2027, so it’s not going to be an easy contract to move, but if the White Sox are willing to eat a majority of the money, perhaps someone could use a serviceable DH against right-handed pitching. Moving Benintendi would free up a roster spot and give the White Sox the option to move Sam Antonacci or Munetaka Murakami to DH, opening up a spot in the lineup and potentially giving the opportunity to an outside addition or internal promotion. If they are able to move Benintendi, I would expect an insignificant prospect return in exchange, with the salary relief and open roster spot being the primary benefit. Perhaps a rookie ball lottery ticket is the best they can hope for.
Andrew Benintendi and the @WhiteSox retake the lead in the 8th! pic.twitter.com/eHapkNaXej
— MLB (@MLB) August 18, 2026
IF/OF Luisangel Acuna
When the White Sox first acquired Luisangel Acuna in the trade that sent Luis Robert Jr. to the Mets last offseason, they hoped to get more out of him offensively than he’s provided in recent years. Acuna began the season as a direct replacement for Robert, starting in center field. After some struggles and the emergence of Tristan Peters, Acuna was thrown into more of a bench role, typically getting starts against left-handed pitching and pinch running late in games. As the White Sox look to build a roster for next year, it’s hard to justify keeping Acuna on the team, and he’s out of minor league options. Brenton Doyle provides the same speed and defense skillset off the bench that Acuna does and seems to have more offensive upside. I think moving on from Acuna and looking for another bench infielder would be wise. Jorge Mateo is a name that peaks my interest. If the White Sox choose to go this route, they may be able to find a team looking for infield depth and speed on the bench and find a trade partner for Acuna. With Chicago looking for arms, perhaps swapping Acuna for a reliever on the 40-man bubble could make sense for both sides. Regardless, i don’t need to see him on the Opening Day roster in 2027
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