Not only were the Chicago White Sox leading the AL Central rather comfortably by the time the trade deadline rolled around, but they were in position to earn the No. 2 seed in the American League, ensuring them a first-round bye. A big trade deadline would've all but gifted them a bye, but instead, the White Sox underwhelmed and have played uninspired baseball ever since.
Now, even after their win on Saturday, Chicago trails the Cleveland Guardians in the AL Central and is narrowly holding onto a playoff spot as the third Wild Card team. These trade deadline mistakes are the reason why the White Sox are barely holding on for dear life rather than establishing themselves as true contenders.
Refusing to trade away top prospects
The White Sox made it clear from the onset that they were unwilling to trade the best prospects in their farm system, and to this day, I have absolutely no idea why they had that mentality. Sure, their season was already a success to an extent, as they were clearly going to blow past initial expectations, but didn't they have any desire to go on a deep playoff run? Were they really satisfied with just a simple playoff appearance?
I'm not saying they had to trade Caleb Bonemer, and Hagen Smith has been a key contributor down the stretch, but had the White Sox expressed a willingness to trade any of their top prospects for a needle-mover, the tone surrounding this team might be completely different.
Not adding a legitimate frontline starter
Speaking of the refusal to move prospects, the White Sox really missed the boat when it came to fortifying their rotation. Heading into the month of August, the White Sox ranked dead last in innings pitched by their starters. Since August 1, the White Sox are not only dead last in innings pitched by their starters, but they are more than 30 innings below the next-worst team in that category. Their 5.70 ERA is the fourth-worst in that same span. That is a problem.
Not getting any sort of length or effectiveness from starters puts an enormous amount of pressure on the bullpen to pitch incredibly well. To their credit, this White Sox bullpen has been mostly stellar, but at a certain point, they're going to run out of gas. That's on Chris Getz for not acquiring a single starting pitcher they can rely on to eat innings at any point. Parting with a good prospect for rotation stability would've been more than worth Chicago's while.
The Luis Castillo trade
The one starting pitcher the White Sox did acquire was Luis Castillo, whom Chicago essentially got in a bad contract swap, with Seranthony Dominguez heading to Seattle. This deal made some sense at the time, as while Castillo wasn't the star he once was, he could seemingly be a decent enough innings eater for them. Clearly, that has not been the case.
Castillo posted a 7.52 ERA in his first six starts after the trade, prompting the White Sox to move him to the bullpen. Early returns in that role aren't so great either, with Castillo allowing three runs in 2.2 innings of work. Sure, he didn't cost much to acquire trade-wise, but the White Sox owe him $24.1 million next season and he has a $25 million vesting option for 2028 as well. Again, trading prospect capital for reliable starting pitching would've been wise.
Not acquiring a big right-handed bat
Another need that the White Sox had entering the deadline was a right-handed bat. Sam Antonacci, Kyle Teel, Munetaka Murakami, Tristan Peters and Colson Montgomery are all solid options, but they're also all left-handed. Miguel Vargas is a star right-handed bat, but who is their second-best right-handed hitter? Chase Meidroth? The White Sox made a trade for a right-handed bat, but it was for Brenton Doyle, a defense-first outfielder who had a .569 OPS before the trade. He's been better with the White Sox but is still well below average at the plate.
The White Sox have been playing guys like Doyla, Tommy Pham, Luisangel Acuña and Jake Rogers against lefties because Chris Getz, for whatever reason, did not acquire a big righty bat. I know those were scarce, but the White Sox could have and absolutely should have done better here. The White Sox's offense struggling in the month of September isn't solely because of Getz not getting a big right-handed bat, but ignoring that need certainly hasn't helped matters.
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