Cubs Deadline Pitching Push Looks Different With October Closing In

As the Cubs' playoffs approach, mixed results and promising trades generate debate over the team's bold trade deadline strategy.

The Cubs went into the deadline looking for pitching, and they did not tiptoe around the market. They made a handful of aggressive moves, loaded up on arms, and now the question hanging over all of it is simple: did Chicago actually improve enough to make this run matter?

Kevin Gausman was the headliner, the first front-line starter the Cubs brought in. The 35-year-old arrived with real expectations and, so far, mixed results.

He has posted a 5.04 ERA in eight starts and 44.1 innings with Chicago, a step down from the 4.38 ERA he carried over 23 starts with Toronto before the deal. September has been all over the place for him: he opened with a seven-inning gem against the Milwaukee Brewers, giving up one run, then got shelled by those same Brewers for six earned runs in four innings in his next outing.

He bounced back against the Atlanta Braves with 5.2 innings and two earned runs. The real test, though, is still ahead.

In 14 years of playoff baseball, including a World Series run with the Blue Jays last season, Gausman owns a 3.83 ERA in 56.1 innings.

Chicago sent Ty Southisene and Brett Bateman to Toronto in that deal. Southisene is now the Blue Jays’ No. 17 prospect and is hitting .262 with an .809 OPS in High-A.

Bateman has already reached the majors and settled into an everyday outfield role for Toronto, where he’s hitting .320/.394/.413 with an .807 OPS. The Cubs clearly decided there wasn’t room for a 24-year-old center fielder on their roster - especially with one already in house who, as the piece notes, is pretty good.

Clay Holmes was the other big swing, and that one has been a study in extremes. Holmes spent much of the early part of the season on the IL after suffering a shin fracture from a comebacker, so his 2026 sample size was limited when Chicago went after him.

In August, he looked every bit the part, putting up a 1.55 ERA in five starts and 29 innings. September has been a different story.

Over three starts this month, he’s allowed 16 earned runs in 15.1 innings, and the Cincinnati Reds hit him for six earned runs in his most recent outing.

Still, the Holmes trade may be remembered just as much for Tyrone Taylor. He’s been exactly the kind of platoon bat the Cubs hoped for and maybe more.

Chicago tried this kind of move last year with Willi Castro, and that experiment flopped badly; Castro hit .170 with a .485 OPS in 34 games. Taylor has been the opposite.

In 28 games with the Cubs, he’s slashing .343/.387/.493 for an .879 OPS and has already been worth 0.9 bWAR. Holmes, by comparison, is at 0.3.

Jefferson Rojas was once the Cubs’ No. 1 prospect, and he’s put together a strong showing since the deal, though it’s happening for the Mets and not Chicago. The 21-year-old infielder hit .308 with a 1.037 OPS in Triple-A after the trade, and he could be in line to make his big-league debut by Opening Day next season. It’s still too early to know exactly what he becomes, but for now the impact in this deal clearly leans toward Holmes and Taylor for a Cubs team trying to push through October.

Braxton Garrett is another case where the verdict remains fuzzy at best. When Chicago got him from Miami, he had thrown only 4.1 big-league innings all season, all of them in May, and his ERA sat at 14.54.

He had at least looked better at Triple-A for Miami, where he posted a 2.90 ERA in 77.2 innings, but the Cubs have yet to see him in the majors. He’s struggled at Triple-A Iowa as well, with a 4.11 ERA in 30.2 innings.

Garrett is under team control through 2028, so the path forward is still there, but right now this one looks like a quiet trade. Chicago gave up former No. 13 prospect Jonathon Long and six-foot-9 right-hander Jace Beck.

Long hit .275 with 16 homers and an .816 OPS across Triple-A stops with the Cubs and Marlins, while Beck struggled in Triple-A for both organizations, posting a 6.60 ERA with the Cubs and a 6.66 ERA with the Marlins.

Ryan Zeferjahn has also been a mixed bag. The Cubs brought him in as a hard-throwing, strikeout-heavy reliever under control through 2030, and the pitch mix still makes sense on paper.

The results have not always matched the profile. In 16.1 innings with Chicago, he has a 4.96 ERA, up from 3.66 with the Angels, along with a 1.53 WHIP after sitting at 1.20 before the trade.

He has also blown two saves in 18 appearances. But there is at least some momentum there now: over his last seven games, Zeferjahn has worked to a 1.42 ERA and picked up two saves.

Then there’s Moises Ballesteros, who drew plenty of attention because Cubs fans liked him and because Mason McGwire, son of Mark, was also included. Ballesteros has received a more regular role with Los Angeles, but the bat has not really taken off. Since the trade, the 21-year-old is hitting .208 with a .560 OPS.

The deadline haul was big, the intent was obvious, and the early returns have been uneven. Some pieces have flashed, some have stalled, and some are still waiting for a real chance. With the NL Wild Card Series only days away, the Cubs are about to find out which version of this deadline actually travels in October.

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