Cubs and White Sox Trade Deadline Breakdown — Thumbs Up, Thumbs Down Edition

OVER THE MLB TRADE DEADLINE LONG WEEKEND, neither the Cubs nor the White Sox entirely revamped their rosters — but they came damn close.

Their respective plethora of deals reset our expectations for their respective postseason chances, with the North Siders overhauling their starting rotation and the South Siders making some notable tweaks all over the field.

Being that this here baseball dumbass doesn’t quite get what all of this overhauling and tweaking might amount to, I did what I always do when I need some incisive MLB commentary and turned the column over to MLB Daily Dingers’ Editor in Chief Matt Musico, who explained to me in plain English which moves merited a thumbs up, or a thumbs down, or a bit of both.

• Kevin Gausman (RHP)

• Brett Bateman (OF)

• Ty Southisene (IF)

I love this move and how the Cubs added a ton of pitching to their roster for the stretch run. As Alan said yesterday, Gausman hasn’t necessarily been at his best recently, but the track record is there. Outside of this season, he hasn’t posted an ERA higher than 3.83 since 2018. And even more importantly, you can pencil him in for 170-plus innings in recent years.

You also can’t discount his postseason experience, especially after just reaching the World Series with the Blue Jays last year. I wouldn’t be surprised if the Cubs have some tweaks to suggest to him upon getting to the Windy City, similar to how they helped David Peterson turn things around.

• Cash Considerations

• Player To Be Named Later

• Jameson Tallion (RHP)

• Cash Considerations

Getting some cash and a player for someone you just DFA’d? Nicely done. May end up being nothing, but at least there’s a chance for something.

• Braxton Garrett (LHP)

• Jace Beck (RHP)

• Jonathon Long (IF/OF)

This is another one where you have to believe the Cubs see something that they can change or tweak. Garrett is still only 28, and while he owns a 6.31 ERA since the start of 2024, he’s only tossed 41.1 total innings and missed all of 2025. The potential was shown from 2022-23 when he posted a 3.63 ERA with 246 strikeouts across 247.2 innings.

He does have a 2.90 ERA across 77.2 innings in Triple-A this season. It always scratches your head when a team gives up two players for one pitcher that hasn’t had a ton of recent success, but do you know what every contender needs down the stretch? It starts with a “P” and rhymes with “itching.”

This is a depth move, and it doesn’t hurt that Garrett is left-handed.

• Ryan Zeferjahn (RHP)

• Moises Ballesteros (C/DH)

• Mason McGwire (RHP)

Bolstering the starting rotation is important, but for teams eyeing a postseason run, a strong bullpen is essential. And when you can call upon a dude who can throw hard and make hitters swing and miss? Chef’s kiss.

Speed is what Zeferjahn has delivered this year, boasting a 33.5% strikeout rate and an average fastball velocity of 97.5 mph across 51.2 innings for the Angels. He’s also gotten some experience closing games, racking up four saves after managing just two in 2025.

Watching Mo Baller leave town is probably tough for Cubs fans to stomach, but you’ve gotta give up something good to get what you need. Zeferjahn won’t be arbitration-eligible until 2028, either.

• Clay Holmes (RHP)

• Tyrone Taylor (OF)

• Jefferson Rojas (IF)

Rojas was the Cubs’ no. 2 prospect, but he’s in Double-A, and he won’t help the Cubs make a deep postseason run this year. You know who could? Clay Holmes and Tyrone Taylor, that’s who.

Holmes is coming off a serious injury, but he provides flexibility because he’s racked up successful innings as both a starter and reliever in New York, so he knows how to play in a big market.

As for Taylor, he’s a perfect kind of fourth outfielder. While his stats with the Mets won’t necessarily jump off the page, he can play all three outfield positions and provide some offense.

• Luis Castillo (RHP)

• Seranthony Domínguez (RHP)

• Nolan Jones (OF)

• Boston Smith (C/OF)

I love this move for the White Sox. You can see that Castillo hasn’t had the best season, but there have also been times when he and the Mariners coaching staff/front office haven’t agreed with his usage.

He’s a dependable veteran who you can count on to take the mound just about every fifth day. I think he needed a change of scenery, and the rest of the rotation should benefit from his experience. According to FanGraphs’ Roster Resource, Castillo has racked up just over eight years of MLB service time, which includes three trips to the postseason since 2020.

The rest of Chicago’s big-league pitching staff has racked up just over four years of big-league service time…combined.

• Huascar Brazoban (RHP)

• Gabe Davis (RHP)

• Zach Franklin (RHP)

Seranthony Domínguez was part of the package to acquire Castillo, so I do like how the White Sox turned right around and acquired Huascar Brazoban from the Mets to take his place in the ‘pen.

Dominguez was signed through 2027, but Brazoban can be under team control through 2030. He was one of the Mets’ more consistent relievers throughout the first part of 2026, racking up a 2.56 ERA, 1.006 WHIP, and 49 strikeouts across 52.2 innings.

• Brenton Doyle (OF)

• Mason Adams (RHP)

• Carlos Vielma (IF)

This is an interesting move. Doyle looked like a budding star in Colorado after slugging 23 homers with a .764 OPS in 2024 — however, he hasn’t been able to recreate that offensive production since. His numbers have cratered in 2026, plummeting to to a .569 OPS with one homer and a -0.4 bWAR across 45 games played.

But the 28-year-old brings some centerfield defense to the South Side. His 20 Outs Above Average (OAA) since the start of 2024 ranks eighth among qualified MLB center fielders is one of the reasons he’s a two-time Gold Glove Award winner.

If I were Sox skipper Will Venable, I’d want him to get comfortable playing all three outfield positions over the next couple of months, which is something Doyle hasn’t done at the big-league level.

Maybe this is a long-term, low-risk, high-reward reclamation project, but it’s hard to envision Doyle instantly kicking it into high gear after a couple of tough seasons.

• Joey Bart (C)

• Duncan Davitt (RHP)

Despite his top-prospect pedigree, acquiring Joey Bart probably isn’t going to give Sox Nation the warm tinglies. After all, he’s hitting .226/.303/.377 with four homers and 13 RBI across 119 plate appearances split between the Pirates and Braves.

But the White Sox have gotten nothing out of this position all year. Kyle Teel has been limited to just 70 plate appearances after a solid rookie campaign, and Chicago’s collective -1.1 fWAR out of their catchers is the worst in baseball, according to FanGraphs.

You have to hope Bart gives them more production than they’ve gotten with consistent playing time while waiting for Teel to return. Then again, he won’t have to do much to potentially be an asset.

There were definitely better options available out there, but obviously at a steeper price…but least the Pale Hose found someone.

OVERALL, it was a good trade deadline for the Cubs. They had a clear plan to beef up their pitching staff, and that’s exactly what they did.

I also liked the Sox’ deadline. Nobody initially expected them to be buyers at any point this year, and it’s nice to see them make some moves that will hopefully help sustain them down the stretch. The Guardians also had a sneaky-good deadline, so the AL Central race should be a whole lot of fun.