The Chicago White Sox had a disappointing end to what was a miraculous turnaround for the franchise. Now that the season is over, changes must be made to turn the team into a true contender. And starting pitching is the most obvious need for Chicago.
Luis Castillo was the only starter acquired by Chicago at the trade deadline, and he has been a disaster thus far. Due to this swing-and-miss at the deadline, the White Sox will once again need to add in the offseason. There should be many starting pitchers with control on the move, but who could the White Sox trade to help fill this hole?
Aug 29, 2026; Minneapolis, Minnesota, USA; Chicago White Sox designated hitter Andrew Benintendi (23) hits a solo home run against the Minnesota Twins during the sixth inning at Target Field. Mandatory Credit: Nick Wosika-Imagn Images | IMAGN IMAGES via Reuters Connect
Designated hitter Andrew Benintendi is coming off a somewhat strong 2026 season. In 141 games, Benintendi slashed .240/.302/.413 with 15 home runs and 78 runs driven in while platooning with Randal Grichuk. However, Benintendi's White Sox tenure has not been what the team envisioned when they signed him to a five-year, $75 million deal, accumulating a 0.5 bWAR in four seasons. His lack of production in the postseason also necessitates a parting of ways.
Now that Grichuk is a free agent, the White Sox may have to choose between him and Benintendi. The former Gold Glove outfielder has been limited to designated hitter duties after being virtually unplayable in left field. Due to this, it's hard to justify having him on the roster moving forward.
Benintendi will be owed just over $15 million in 2027, entering his age-33 season, which will be his last on his current contract. The former All-Star could be moved to either shed payroll or packaged with a prospect to take on a starter's contract.
Sep 9, 2025; Chicago, Illinois, USA; Chicago White Sox 2025 draft pic Billy Carlson throws out a ceremonial pitch before the teams game against the Tampa Bay Rays at Rate Field. Mandatory Credit: Matt Marton-Imagn Images | IMAGN IMAGES via Reuters Connect
When the White Sox drafted Billy Carlson 10th overall in the 2025 MLB Draft out of high school, the future of the infield was a lot less certain. Colson Montgomery hadn't debuted yet, Miguel Vargas, and Chase Meidroth didn't have their breakout seasons. Munetaka Murakami also wasn't signed, and Roch Cholowsky wasn't drafted.
Now, there is significant crowding in the infield. Carlson is still incredibly young (20 years old), and his potential is there. He was regarded as the best defensive shortstop prospect in decades (maybe even ever), and has lived up to that standard thus far. In 60 minor league games, Carlson slashed .252/.380/.335, but he has struggled in the power department with no home runs.
Carlson is currently the No. 81 prospect in the game. While it's hard to let go of a prospect of his caliber, especially one with his defensive acumen, Chris Getz has to acquire starting pitching at any cost this offseason. If the White Sox can package Carlson for a quality starting pitcher with control, Getz has to pull the trigger to ensure the 2027 White Sox don't share the same fate as the 2026 team.
Oct 8, 2026; Chicago, Illinois, USA; Chicago White Sox center fielder Brenton Doyle (7) celebrates during the fifth inning against the Cleveland Guardians in game four of the ALDS for the 2026 MLB Playoffs at Rate Field. Mandatory Credit: Matt Marton-Imagn Images | IMAGN IMAGES via Reuters Connect
It was a bit of a head-scratcher when the White Sox acquired outfielder Brenton Doyle from the Colorado Rockies in exchange for pitching prospect Mason Adams. While Doyle had his moments in a White Sox uniform, slashing .258/.258/.462 with five home runs, he struggled in the postseason with a .349 OPS. He was great against left-handers but struggled against right-handers. The two-time Gold Glove outfielder's defense was solid as usual, but the White Sox's influx of outfielders leaves Doyle on the outside looking in.
The White Sox already have Braden Montgomery, Sam Antonacci, and Tristan Peters in the outfield. No. 27 MLB prospect Caleb Bonemer has also been training in center field, likely preparing for an Opening Day spot. While Doyle provides some offensive value and great defensive value, you can't just hold onto him as a defensive replacement when he likely won't get many at-bats.
The team is going to have to make some difficult decisions this offseason, and while Doyle isn't a free agent until after the 2029 season, he may be the odd man out.
This article was originally published on www.si.com/mlb/whitesox/onsi as 3 White Sox Players Who Could Be in Trade Rumors This Winter .
