The White Sox have spent much of this season forcing people to rethink them. At 54-47 and sitting atop their division heading into the weekend, they’ve already done the surprising part. Now comes the harder one: building a rotation that can actually hold up in October.
That’s why the trade market matters so much for Chicago right now. The Sox have been tied to a number of pitchers over the past couple of months, but not every arm on the board is worth the price.
One option looks too shaky. Another looks like the kind of short-term move that makes real sense.
Clay Holmes is the kind of name that can tempt a front office, but the White Sox should stay away. MLB.com reported that Chicago is among the teams keeping an eye on him, yet the injury history changes everything.
Holmes was hit by a line drive in May and fractured his right fibula. He began a rehab assignment Thursday at Triple-A and allowed two runs on three hits while walking two and striking out two over 2 1/3 innings.
He’s expected to need at least one more rehab outing before returning, and that’s part of the problem. Before the injury, Holmes posted a 2.39 ERA, which makes the idea of a deal look attractive on paper.
But the Sox don’t have the luxury of gambling on a pitcher who is still working his way back and may need more time to get right. Chicago needs help soon if it wants to keep the gap between itself and the Guardians from shrinking.
There’s also the contract wrinkle: Holmes can opt out after the season. Trading for a banged-up pitcher who might only be available for a couple of months is a tough sell.
Brady Singer, on the other hand, looks like the more practical bet. A 4.53 ERA doesn’t jump off the page, but his recent stretch does.
Over his last eight games, he has put up a 2.76 ERA, and his breaking ball has been doing real work while he’s kept walks in check. Singer got off to a rough start, but his value has been climbing.
For a team thinking about the postseason, that matters. The White Sox need pitchers who can take the ball and give them innings, and Singer fits that description.
He’s owed only $4 million for the rest of the season, which makes him a clean short-term solution. Holmes might be the better pitcher when healthy, but Singer looks like the safer one to trust for steady work right now.
If Chicago goes after Singer, that doesn’t have to be the end of the shopping. The Sox could still add another controllable starter, with Reid Detmers and Jose Soriano of the Angels mentioned as bigger-name possibilities. A move like that would give Chicago more stability in the rotation and still leave room to turn to the relief market afterward.
However they do it, the assignment is clear: add veteran pitching. Whether the White Sox land one impact starter or a pair of dependable arms, the rotation is the priority. What they do at the deadline will say plenty about how far this team can go.
In Other News...
White Sox Prospect Rankings Just Took An Unexpected Turn
MLB Pipelines latest White Sox top-30 prospect update brought a few familiar names into sharper focus, but the most notable shift was Boston Smith cracking the list at No. 15 after entering unranked before. The refreshed rankings also reflect how much the system has changed in recent weeks, with Braden Montgomery, Noah Schultz and Sam Antonacci all having moved on to new levels, leaving the organizations prospect picture in a different place than it was not long ago.
The list is still a little unfinished, though, because it does not yet account for the White Soxs 2026 draft class while the signing deadline remains ahead. That means Caleb Bonemer is sitting atop the board for now, even as the next wave of talent looms, and he also had another rough moment in Birmingham when he was hit in the helmet again after striking out and had to be replaced. [Read more 🡒]
White Sox Top Prospect Sparks Concern After Frightening Exit
Fridays minor league slate was a mixed bag for the White Sox system, which split its six games while a few bats kept the day from becoming a total wash. Korey Lee, Jason Matthews, Boston Smith and Anthony DePino all went deep for their affiliates, giving the organization some offense to point to on a day when several of the headlines were scattered across the farm.
The most jarring moment came when Caleb Bonemer was hit in the head by a pitch and left the game, a frightening scene for one of the clubs top prospects. Preliminary tests were encouraging, but he remains under evaluation, leaving the White Sox with a familiar minor league concern: the results on the scoreboard matter less than the health update that follows. [Read more 🡒]
White Sox Could Finally Make A Future Shaping Deadline Swing
The White Sox are heading toward the trade deadline with a different kind of urgency than the one that usually comes with a rebuilding club. Rather than shopping only for short-term fixes, they are reportedly open to making a more aggressive move for players who come with contract control, the kind of deal that could matter well beyond this season. That approach fits a team still trying to shape its next competitive core, and it gives the front office a chance to chase upside instead of simply filling holes.
There are a few paths they could explore, including arms from the Angels and a potential impact bat from the Athletics, but the challenge is obvious: controllable talent rarely comes cheap. Even when a player looks attainable, the price tag and the odds of a deal actually getting done can be very different things. For a White Sox club trying to balance patience with progress, this deadline could be the first real test of how bold it wants to be. [Read more 🡒]