Re-Grading Every Cubs Trade Deadline Move as The Playoffs Near

When teams are buyers at the MLB trade deadline, it typically means they have their sights set on playoff baseball.

The Chicago Cubs had one of their more aggressive trade deadlines in recent memory this season. They needed pitching, and they got a lot of it. At the time, we gave each move an instant grade.

Now, the NL Wild Card Series is just days away. Was this the trade deadline that takes the Cubs to the promised land, or did they get fleeced (as the kids say)?

Cubs receive: RHP Kevin Gausman

Sep 9, 2026; Milwaukee, Wisconsin, USA; Chicago Cubs pitcher Kevin Gausman (12) during the game against the Milwaukee Brewers at American Family Field. Mandatory Credit: Jeff Hanisch-Imagn Images | IMAGN IMAGES via Reuters Connect

Kevin Gausman was the first front-line starter that the Cubs acquired at the deadline. The 35-year-old, who will become a free agent after this season, hasn't exactly performed to the expectations set upon him when he first put on Cubs pinstripes.

Some may recall that Gausman was projected to lead the Cubs in WAR for the rest of the season. That prediction hasn't quite panned out -- Gausman has a 5.04 ERA in eight starts and 44.1 innings since joining the Cubs. He had a 4.38 ERA in 23 starts with Toronto in the first half.

Gausman has had a roller coaster month of September, which began with a masterful seven-inning outing against the Milwaukee Brewers in which he allowed just one run. But the Brewers figured him out in his very next start, lighting him up for six earned runs in four innings.

Gausman returned to form against the Atlanta Braves, going 5.2 innings and allowing two earned runs.

What will be most intriguing for Gausman is how he fares in the postseason with the Cubs. He has a 3.83 ERA in 56.1 innings of playoff baseball in his 14-year career, which includes a World Series run with the Blue Jays last season.

Blue Jays receive: INF Ty Southisene, OF Brett Bateman

The Cubs gave Toronto two prospects in return: Ty Southisene and Brett Bateman. Southisene is now the Blue Jays' No. 17 prospect, and he's hitting .262 with an .809 OPS in High-A since joining his new organization.

Bateman has since made his MLB debut, and he's carved out an everyday role in the outfield in Toronto. He's slashing an impressive .320/.394/.413 (.807 OPS) and could have been a surefire Rookie of the Year candidate if he had had such a role for the entire season.

The Cubs clearly felt there wasn't a pathway on the big-league roster for a 24-year-old center fielder -- they have one of those already, and he's pretty good!

Our instant grade: B+
Re-grade: B

Cubs receive: RHP Clay Holmes, OF Tyrone Taylor

Aug 25, 2026; Phoenix, Arizona, USA; Chicago Cubs pitcher Clay Holmes in the first inning against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images | IMAGN IMAGES via Reuters Connect

The Cubs took a big swing to get Clay Holmes at the deadline. Holmes' 2026 sample size was small after he spent most of the beginning of the season on the IL with a shin fracture from a comebacker.

In August, Holmes was everything the Cubs could have asked for. He pitched to a near-spotless 1.55 ERA in five starts and 29 innings. But the 33-year-old has struggled in his three starts this month, allowing 16 earned runs in 15.1 frames. The Cincinnati Reds tagged him for six earned runs last time out.

The funny thing about the Holmes trade is that the sidecar has almost had more of an impact. It was hard to predict what Tyrone Taylor was going to do as a Cub, but he's been the platoon bat of dreams for a team that has tried this recipe before.

Last year, they tried it with Willi Castro and things just didn't go well at all. Castro, who came from the Minnesota Twins, batted .170 with a .485 OPS in his 34-game stint.

Taylor, on the other hand, has been a revelation: He's slashing .343/.387/.493 (.879 OPS) in 28 games since coming to Chicago with Holmes. He's already worth 0.9 bWAR as a Cub (Holmes is worth 0.3).

Mets receive: INF Jefferson Rojas

Jefferson Rojas was once the Cubs' No. 1 prospect, so it's not surprising at all to see him tear it up in Triple-A for the Mets. The 21-year-old infielder hit .308 with a 1.037 OPS after the trade, and we could very well see him suit up for the big-league Mets by Opening Day next season.

Since Rojas hasn't reached the big leagues yet, it's hard to tell how he'll pan out. Mets fans probably said that about Pete Crow-Armstrong too, but hey, hindsight is always 20/20. For now, we're focusing on the impact Holmes and Taylor have had on a team making a playoff run.

Our instant grade: A-
Re-grade: A

Cubs receive: LHP Braxton Garrett

May 19, 2026; Miami, Florida, USA; Miami Marlins starting pitcher Braxton Garrett (20) delivers a pitch against the Atlanta Braves during the first inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images | IMAGN IMAGES via Reuters Connect

This was always going to be a head-scratcher. When the Cubs acquired Braxton Garrett from the Miami Marlins, he had only pitched 4.1 innings this season. They all came in May, and he had a 14.54 ERA to boot.

The 29-year-old posted a 2.90 ERA in 77.2 innings with the Marlins' Triple-A affiliate. But he has yet to make a big-league appearance for the Cubs and has struggled comparatively at Triple-A Iowa with a 4.11 ERA in 30.2 innings.

Garrett is under team control through 2028, so it will be interesting to see whether or not he has a path to the roster. But for now, this trade was a bit of a nothingburger.

Marlins receive: INF Jonathon Long, RHP Jace Beck

The Cubs sent former No. 13 prospect Jonathon Long and six-foot-9 right-hander Jace Beck to Miami in return for Garrett. Long hit .275 with 16 homers and an .816 OPS in combined Triple-A stints with the Cubs and Marlins.

The Cubs signed Beck to a minor league contract last offseason, but he struggled in Triple-A for both the Cubs (6.60 ERA) and the Marlins (6.66 ERA).

Our instant grade: B-
Re-grade: D+

Cubs receive: RHP Ryan Zeferjahn

Aug 11, 2026; Washington, District of Columbia, USA; Chicago Cubs pitcher Ryan Zeferjahn (56) walks to the dugout after being removed from the game against the Washington Nationals during the eighth inning at Nationals Park. Mandatory Credit: Geoff Burke-Imagn Images | IMAGN IMAGES via Reuters Connect

It's been puzzling to see Ryan Zeferjahn struggle the way he has with the Cubs.

The reliever was touted as a diamond-in-the-rough deal with the Los Angeles Angels -- a hard-throwing strikeout machine under club control through 2030.

Zeferjahn's 16.1-inning stint with the Cubs has thus far been underwhelming. He has a 4.96 ERA in pinstripes, up from 3.66 with the Angels. His WHIP is up to 1.53 from 1.20, and he's blown two saves in 18 appearances.

Needless to say, there's still a lot of room for growth. Zeferjahn has, in fact, been pretty lights-out over his last seven games, to the tune of a 1.42 ERA and two saves. If he pitches like that in the postseason, so be it. Cubs fans will quickly forget about those rocky few nights on the mound in August.

Angels receive: C/1B Moises Ballesteros, RHP Mason McGwire

Moises Ballesteros was a fan favorite in his short time with the Cubs, which is probably why the initial reaction to the trade was met with some doubt. The up-and-coming Mason McGwire, son of MLB legend Mark, was also part of the deal.

Ballesteros has gotten more of an everyday role in Los Angeles, but he's struggled even more than he did at the tail-end of his Cubs career. The 21-year-old is hitting just .208 with a .560 OPS since going out west.

Our instant grade: C+
Re-grade: B+

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