How the White Sox Can Succeed at the Trade Deadline

While most focus on the teams getting ready to bolster their roster ahead of a (hopeful) deep playoff run this October, I’m thinking about how the Chicago White Sox can extract the most value possible from their roster via trades.

This season has been, dare I say, fun (ish?) in Chicago despite the White Sox still being one of the worst teams in baseball. After losing the most games in MLB history last year, a record which may be broken soon in Colorado, there are signs of growth in 2025.

The White Sox have leaned into the future this season, and it’s showing. It’s no longer a falsified effort to compete, but rather a genuine *silent* acknowledgment that the focus is 2027 and beyond.

Players such as Edgar Quero, Colson Montgomery, Kyle Teel, Grant Taylor, and others have become the focal point of this roster.

The roster is young but still features several veterans who could be moved this week. While there are no players that will net a return even close to the White Sox haul for Garrett Crochet, they can keep adding assets to the core.

It’s unlikely to be a particularly exciting deadline for Chicago, but there are a few key steps that can be taken to further improve the system heading into 2026.

Move on From Luis Robert Jr.

His value is nowhere near where most would have imagined a year or two ago, but I still think it’s time for the White Sox to trade their center fielder.

A lot of people have started to consider the idea of the White Sox keeping Robert, given his brutal numbers over the past year and a half. But that would mean either the White Sox picking up a $20 million option for next season or paying the buyout to let Robert walk.

With nearly the whole core from the last contending White Sox team gone now, it’s time to move on from the final member.

The return will be worse than White Sox fans want, but it’s hard to justify paying Robert $20 million next season with the hope of him reclaiming some value.

If they can net one solid prospect and a second flyer piece for Robert, that’s a deal that should be made.

The Mets and Phillies still seem like the best fits for Robert, as they could use a center field upgrade and can afford some of the risk that comes with Robert.

Netting a top 10-15 prospect within either system, in addition to a possible flyer, would satisfy me even though it will feel understandably disappointing to most White Sox fans.

Cash In on Adrian Houser

Every team needs pitching at the deadline, and the White Sox found a veteran pitcher who is putting together the best season of his career.

Adrian Houser, who was signed in May, has been a revelation in the Chicago rotation. He has been the best pitcher on the roster and will be an appealing trade target given his affordability and performance to this point.

These types of signings that can be flipped are the ones that help accelerate a rebuild. Getting anything in return here is a win, but Houser may net a very solid prospect. He has a 2.10 ERA through 11 starts, which could make him a target of many teams.

Essentially every contender could use a starter, but a few teams stand out as clear fits for Houser. Houston, San Diego, Detroit, and Toronto seem like logical fits to me.

Chicago can take advantage of the market this season with not many clear sellers and particularly few with good starters.

Getting a quality hitting prospect who can help in Chicago in the next year or two in exchange for Houser would be the ideal scenario.

Package Veterans to Net Prospects

Beyond Houser and Robert, the White Sox have various veterans who can be moved but won’t return much of substance.

To maximize the prospects coming back to Chicago, packing veterans together is probably the best way to go.

Mike Tauchman is probably the next most intriguing trade chip, especially given he has another year of control. He has been a productive piece of the lineup all season with an .840 OPS but is still ultimately a 34-year-old corner outfielder.

Michael A. Taylor and Austin Slater were both signed to add depth to the outfield and have been decent pieces at times. Slater will appeal to teams looking for a weak-side platoon hitter who can mash lefties, while Taylor fits well as a fourth outfielder who can be trusted defensively.

That trio of outfielders will receive interest, and I expect at least one or two of them to be moved. A number of relievers could be on the move too, despite none really standing out.

Steven Wilson could be the most appealing with two more years of control beyond this season, but he’ll come at a steeper cost. Dan Altavilla, Tyler Alexander, Brandon Eisert, and Tyler Gilbert may all get dealt.

To get a bit of value from these various veterans, I expect to see packages of two or three veterans sent to a contender looking to fill out their roster. This is probably the way to get at least a couple of decent prospects from any of these veterans.

The more guys in this category that can be traded this week, the better. The White Sox have plenty of relief pitchers ready to slot into the bullpen in Chicago and hitters who could be promoted or start to receive more innings down the stretch.

Future Is Now

This is more of an overarching sentiment in regards to the organization for the rest of the season. It starts with the deadline, though.

Trying to get value for as many veterans as possible will be the aim, but the aim should remain the same if they’re unable to do so.

If veteran players don’t receive interest from other teams, the team should not hesitate to just move on from some players to create roster spots for more young talent.

Bullpen arms like Wikelman Gonzalez, Jairo Iriarte, and Peyton Pallette should all get innings to finish out the year. The young hitters already on the roster should be playing every day and joined by more hitters from Triple-A, such as Will Robertson and Bryan Ramos.

The movement has already started and this deadline leading into the final two months of the year should simply lean into that.