The Chicago White Sox went from 102 losses to 84 wins and an appearance in Game 5 of the ALDS. Elimination Day for most teams is a day of reckoning. For the overachieving White Sox, it’s a sign of better days ahead.
Thanks in large part to a rebuilt farm system as well as some surprising performances, the Southsiders managed to make it a memorable year in 2026. No significant free agents, at least not anyone they couldn’t easily re-sign, are leaving. They can stay largely intact however they wish while adding around.
Last offseason was pretty standard for the White Sox. This time around, they might want to move forward with greater purpose and boldness. These moves can help get them there and make the ALDS the bare minimum.
1. Trade for someone’s disgruntled and available star
Bryce Harper, Ronald Acuna Jr., and anyone else who happens to have become an unexpected trade candidate this offseason should be an option for the White Sox to consider. They made it to Game 5 of the ALDS without any true star players. While not always a necessity, it tends to be an easy singular move to help give your club a makeover.
The troubling part here is knowing who to pick. You don’t want to bring in a guy whose ego will get jammed coming in through the door. Several of these trade scenarios would involve big money contracts moving. Players like Luis Castillo and Andrew Benintendi whose deals are at the top of the White Sox payroll could have desirability if swapped for anyone on a longer deal.
2. Steal the best free agent hitter and pitcher from the Cubs
The crosstown Chicago Cubs have a lot of guys who’ll officially hit the open market after the World Series. Familiarity with the Windy City helps mildly. Moreover, it’s a strong combination of players who can help fill in some White Sox roster gaps.
Whomever they consider to be the best of the Cubs free agents is who the White Sox need to add. Seiya Suzuki had a far better season than Ian Happ in 2026. That significantly boosts one of their weaker overall positions, right field. Playing time will still arrive for Braden Montgomery even with Suzuki on a multi-year deal. Starting pitching provides them with a plethora of choices. Clay Holmes probably makes the most sense, but Shota Imanaga shouldn’t be overlooked. Starting pitching was shallow for the White Sox this season. That’s a spot they must fortify.
3. Fall on the other side of a Chris Sale/Garrett Crochet trade
Chris Sale and Garrett Crochet aren’t exactly Brett Favre and Aaron Rodgers and yet their career trajectories aren’t so dissimilar. They started with the same team and upon leaving, joined the same exact new one. The White Sox were on the seller side of both deals. What about reversing it and becoming the buyer?
Acquiring somebody else’s Sale or Crochet can be an exclamation point on the offseason. By picking up a disgruntled player on another roster, you’re seizing an opportunity while adding money to your payroll. It’s easy to sign Cubs free agents. They’re there for anyone willing to pay. Correctly identifying and trading for a younger pitcher with some years of control is the challenge.
In this regard, the White Sox should look at guys who aren’t making significant money, although they shouldn’t balk at those guys completely. It’s time they become the ones to land a controllable starting pitcher not making a whole lot of cash. Start with another phone call with the Seattle Mariners who could use some offense and have pitching.
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