Key Points
Bullet point summary by AI
- The Chicago White Sox need aggressive trade deadline acquisitions to maintain their AL Central lead over the Cleveland Guardians.
- Mock trades propose acquiring starter Robbie Ray and reliever Keaton Winn, closer Aroldis Chapman, or a frontline ace like Reid Detmers.
- Securing elite pitching arms protects the roster against key division rivals and solidifies a serious run into the postseason.
While the Chicago White Sox lead the way in the AL Central, it's not as if their 2.0-game lead over the Cleveland Guardians is comfortable by any means. For them to overtake Cleveland, especially knowing that Jose Ramirez will be making a return from the IL at some point, they're going to need to improve the roster at the trade deadline.
These three mock trades could be what pushes Chicago over the top of Cleveland and into the postseason.
This White Sox-Giants mock trade would kill two birds with one stone for Chicago
If the White Sox are going to buy, they're going to pursue pitching of all kinds. That means adding to their rotation and their bullpen. This mock trade with the San Francisco Giants would address both needs.
The big name of the deal is Robbie Ray, a former Cy Young winner who, while not quite at that level, is still a viable mid-rotation arm. He has a 3.39 ERA in 17 appearances this season, allowing three earned runs or fewer in all but three of those outings. He's striking out fewer batters than he ever has and has always had inconsistent command, so that ERA is probably bound for some regression, but he's pitched very well of late and is still a veteran stabilizer that the White Sox's rotation could really use.
Keaton Winn isn't a big name, but he's moved to the bullpen full time this season and has excelled, posting a 3.23 ERA to go along with a 3.24 FIP in 29 appearances and 30.2 innings of work. He's currently on the IL with an elbow strain, but he's expected to be back sometime this month. What makes Winn particularly intriguing, in addition to his strong production this season, is that he isn't even hitting arbitration until after next season, so the White Sox would have him under cheap control for quite a while.
This package wouldn't come cheap, as Tanner McDougal is one of their top prospects. However, knowing the White Sox would be acquiring Ray to help them down the stretch and that they have Noah Schultz ready to help out now and fellow top prospect Hagen Smith not far behind, he's expendable. Getting a couple of key months of Ray and several years of Winn could very well be the right kind of deal for Chicago, and with the Giants being likely sellers, this trade would make sense for them, too.
This White Sox-Red Sox mock trade lands Chicago the lockdown closer it needs
While Grant Taylor has been mostly dominant, Seranthony Dominguez is proving to be tough to trust in high-leverage moments, and the White Sox lack any other high-end late-game arms. While they'd probably prefer a right-hander, landing possibly the best reliever available, as this mock trade would have them doing, would be wise.
The White Sox would be landing Aroldis Chapman in exchange for two prospects. Chapman, even at age 38, remains one of the league's best closers, posting a 2.19 ERA in 26 appearances on the year while striking out 30.2 percent of the batters he's faced. He's still an incredibly hard thrower, and the results he's had for over a year in Boston are undeniable.
While Chapman can hit free agency after the year, his $13 million mutual option becomes guaranteed if he reaches 40 innings and passes an end-of-year physical. He's at 24.2 innings of work halfway through the season, so there's a good chance he'll reach that threshold barring injury, ensuring he'd be locked in for next season as well.
With that in mind, the White Sox should have no problem parting with two of their top 10 prospects per MLB Pipeline in Kyle Lodise and William Bergolla Jr. Lodise has a bit more upside of the two as he's more well-rounded, but he's also farther away from the majors. Bergolla doesn't have much power to speak of, but he's in Triple-A and can run like the wind while possessing an excellent hit tool and a solid glove.
The White Sox would be landing an experienced closer who can help fill a need both this year and next without parting with any of their top-end organizational prospects. That sounds pretty good.
This White Sox-Angels mock trade gives Chicago the ace it lacks
This final mock trade is admittedly the least realistic of the three, but if the White Sox really want to make a splash, Reid Detmers is the kind of player they should be targeting. He might be the most realistic needle-mover for them to pursue.
The White Sox are not going to trade for Tarik Skubal, knowing he's a rental. The White Sox won't be trading for Joe Ryan, knowing he's in their division and the Twins would likely prefer to send him anywhere else (if they trade him at all). I'm not sold that the Angels would trade Detmers, but perhaps with a new executive (John Mozeliak) running things, they'd be open to such a deal, especially for this kind of return.
Detmers isn't a big name, and his 3.88 ERA isn't eye-popping, but he has a 2.96 FIP, proving to be one of the unluckiest pitchers in the sport this year. He has an impressive 27.6 percent strikeout rate, he limits walks, doesn't allow many home runs, and he's fourth, trailing only Jacob Misiorowski, Cristopher Sanchez and Cam Schlittler, in fWAR. Is that good? Oh yeah, and he's under control through the 2028 season, meaning Chicago would be acquiring 2.5 years of cheap control of one of the best starters in the American League.
To get a pitcher of this caliber under control for as long as he is, you have to be willing to give stuff up, though, and the White Sox would be doing that. Hagen Smith, a top-five pick from the 2024 MLB Draft, is one of the best left-handed pitching prospects in the sport, and Billy Carlson, a top-10 pick from the 2025 MLB Draft, is one of the best defensive prospects in the league. There's a world in which both of these players become extremely valuable.
For that reason, I can understand not wanting to go through with this from a White Sox perspective, but not only is Detmers a legit frontline arm, but there're enough concerns with Smith (command) and Carlson (hitting) to be willing to trade them in the right deal. Detmers is certainly the right kind of deal. A lottery ticket like Fernando Graterol, a 17-year-old catcher within the top 30 of Chicago's prospect rankings, could be what gets the Angels to accept the deal.
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