Trade Deadline hindsight reveals 3 clear deals White Sox should've made

Choices seem easier in hindsight. You can't know how a player will perform until you actually use him, and any acquisition is automatically a gamble. The White Sox were in a tough position this year, because they were trying to fill holes before the deadline without losing too much of their newfound player depth and prospect capital. Still, it's hard to look at their deadline acquisitions and be pleased, and a lot of their decisions were clearly suspect even before we saw the results.

Ultimately, the Sox brought in four central players. Joey Bart came in as catching reinforcements, RHP Luis Castillo filled a rotation spot, Huascar Brazoban would pitch in mid-inning relief, and they also added outfielder Brenton Doyle for their bench.

Castillo, Brazoban, Bart have all been disappointments, and the latter two are currently on the injured list. Here are three alternative players the White Sox could've gotten who fit the same roles, and could've been acquired for the same depth.

LHP Robbie Ray Instead of Luis Castillo

The White Sox traded Nolan Jones, Boston Smith, and Seranthony Dominguez to the Seattle Mariners for Castillo. Dominguez is a veteran pitcher who has gotten roughed up this season, but is still usable, and Jones was a throw-in who mostly serves as outfield depth. Smith was the centerpiece of this trade; a 40 FV-grade prospect, per Fangraphs, with some upside because he's a catcher with power, and that power has continued with the Mariners.

The Padres got Ray from the Giants in exchange for a prospect package--Miguel Mendez and Joniel Hernandez. Hernandez has a 40+ FV grade on Fangraphs, while Mendez is listed at 45. He has added value because he's a pitcher with very good swing-and-miss numbers and coming off a strong 2025. Smith is a decent one-for-one swap with Hernandez. If the Sox wanted to secure Ray, they would have needed to add another player better than the Dominguez/Jones combo, but not by much.

Maybe they've could packaged Dominguez with someone like Mathias LaCombe (their No. 18 prospect, who's a 40-grade RHP on MLB.com).

As for the return, Castillo had a 5.06 ERA in 99.2 innings pitched when the White Sox got him. Since then, he's put up a 5.89 ERA in four starts (18.1 innings). Ray had a 3.08 ERA over 122.2 IP, and since then he's pitched 20.1 innings in four starts to 3.98 ERA. The crucial thing is that both pitchers have basically matched their pre-deadline performance. The White Sox could have gotten Ray for not much more than they got Castillo, and they could've added a pitcher who has posted better numbers all season, and added a second lefty behind Anthony Kay.

C Hunter Feduccia Instead of Joey Bart

The White Sox traded Duncan Davitt, a right-handed pitcher stashed in Triple-A, for Joey Bart. This wasn't a bad trade by itself. Davitt had 6.22 ERA in Charlotte this year, Bart was having a serviceable season, and the Sox badly needed another catcher. But Bart played three games without recording a hit before landing on the injured list, so the trade went as poorly as possible.

Feduccia had a .646 OPS (80 OPS+, per Baseball Reference) prior to the trade, which is almost identical to the .680 OPS, 86 OPS+ that Bart had. Feduccia has put up a .774 OPS since being traded to the Dodgers. He might not keep up that pace, but he's already played 18 games, which automatically makes him a more valuable player than Bart right now.

The Dodgers gave up bonus pool money and depth-outfielder Jack Suwinski to get Feduccia. Suwinski hasn't played in the majors this year, and only managed a .534 OPS for the Pirates last year. The Sox probably wouldn't be trading bonus pool money, but they could have packaged one of their own depth-outfielders with a mid-level prospect and likely had a similar deal.

RHP Kirby Yates Instead of Huascar Brazoban

Huascar Brazoban was having an excellent year with the Mets (a 2.56 ERA in 52.2 innings) when the White Sox traded Gabe Davis and Zach Franklin to get him. Davis projects as potential starter with a 35+ FV, while Franklin is a major league-ready reliever. Neither are Top 20 prospects.

Yates had pitched 27.1 innings with a 3.95 ERA before the Pittsburgh Pirates traded for him. That's not overly impressive, but it's still palatable, and since the trade he has pitched 11.1 innings to a 2.38 ERA. In contrast, Brazoban has thrown 10 innings to a 6.30 ERA before landing on the 15-day injured list.

The Pirates gave up Kyle Robinson, a Double-A pitching prospect with a 35 FV grade on Fangraphs. The White Sox probably could have traded either Franklin or Davis, rather than both, to bring back Yates. He had lower value because of his age, but that's also a concern for Brazoban--they're 39 and 36, respectively.

Not all of the White Sox trades were bad at the outset, and in some cases, the players they got looked better than the ones I'm suggesting. But it's hard not to look back and wish the Sox had made better choices. There's also still time for Castillo, Bart, and Brazoban to pull things together, especially when the latter two come off the injured list. Maybe these trades aren't total busts, but it's still hard not to imagine what some more successful moves would've looked like

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