Grading each of the Chicago Cubs' moves at the 2026 MLB Trade Deadline

Chicago Cubs President of Baseball Operations Jed Hoyer said it plainly after the MLB Trade Deadline passed.

"Ideally, you don’t trade prospects," he said. "At the same time, we’re here to win."

His actions reflected those words.

Here’s how we graded each of the Chicago Cubs’ moves after the MLB Trade Deadline passed on Monday evening.

Cubs acquire Clay Holmes

Cubs acquire: Starting pitcher Clay Holmes and outfielder Tyrone Taylor

Mets acquire: Jefferson Rojas

This was the move that puts the Cubs in a different atmosphere.

Before the deadline, the Cubs’ rotation was Matthew Boyd, Shota Imanaga, David Peterson, Colin Rea and Javier Assad.

Now, it’s Clay Holmes, Kevin Gausman, Matthew Boyd, Shota Imanaga and David Peterson, with Edwin Cabrera and Ben Brown still potentially figuring into the mix.

This is a playoff-caliber rotation. Holmes excels in getting ground balls, which plays into the Cubs’ favor with their stellar defensive infield. That will play well in the playoffs, especially against teams that don’t have much power. Namely, the Brewers come to mind.

This move gives the Cubs a No. 1 starter in the playoffs.

It also deepens the bullpen. Moving Holmes into the starting rotation means Assad, Rea, Brown or perhaps even Cabrera might move into the bullpen, allowing Craig Counsell to mix and match whatever he sees fit.

Beyond Holmes, Tyrone Taylor deepens the outfield and can play any position out there. His success against left-handed pitchers gives Counsell a player he can use in a playoff chess match.

This is the kind of move a contender makes. Prospects are the future, but flipping that for players who change the complexion of the pitching staff and add to an already solid outfield is what a contender truly does.

Grade: A

Cubs land starter in Gausman

Cubs acquire: Pitcher Kevin Gausman

Blue Jays acquire: Triple-A outfielder Brett Bateman and Single-A infielder Ty Southisene

This trade goes hand-in-hand with the move to land Holmes. The Cubs get another starter who brings necessary playoff experience to the rotation.

Gausman is a player the Cubs could feel comfortable with handing the ball to start Game 1 of the NLDS. He’s unflappable in the playoffs, as demonstrated in Toronto’s run to the World Series last year.

He’s 36 and is in the last year of his contract, but this is a fantastic deal to add experience and a dominant fastball to a Cubs rotation that needed a change. Gausman gives them that.

Gausman might be a rental, but giving up two prospects – neither of which were considered must-keeps by the Cubs by any means – feels like a steal for the Cubs.

Grade: A

Cubs land reliever Zeferjahn

Cubs acquire: Ryan Zeferjahn

Angels acquire: Catcher Moises Ballesteros and pitcher Mason McGwire

On paper, the Cubs gave up two high-level prospects for a reliever.

Digging deeper here, the Cubs changed the outlook of their bullpen.

Zeferjahn excels in making hitters miss. He has a 3.66 ERA and 75 strikeouts so far this season. In more advanced stats, Zeferjahn a whiff rate of 34.6 percent and a strikeout rate of 33.6 percent. That’s very good.

Much like acquiring Holmes re-shapes the starting rotation, acquiring Zeferjahn re-shapes their bullpen.

Before, Jacob Webb, Trent Thornton and Caleb Theilbar headlined the bullpen heading into August. Now, that bullpen could see Javier Assad, Colin Rea and Ben Brown to it alongside Zeferjahn.

This is a tough move because of the quality of prospects the Cubs gave up to get a reliever. But, this is the kind of move that wins playoffs games.

The Cubs paid for that and for multiple years of team control. If he helps the Cubs win in the playoffs, then it’ll be worth the price they paid.

Grade: A

Cubs send prospects for Braxton Garrett

Cubs acquire: Pitcher Braxton Garrett

Marlins acquire: First baseman Jonathon Long and pitcher Jace Beck

This is an interesting trade to grade. For starters, this isn’t much of a trade that helps the Sky in the 2026 season.

Garrett has pitched 4.1 innings in the majors this year. He has an ERA of over 14. But, he had a stellar 2023 season that’s an example of success at the MLB level before he underwent Tommy John Surgery in 2024 that kept him out for all of the 2025 season.

Garrett is still under team control for a few more years, meaning the Cubs could turn him into a starter for the 2027 season and beyond if they can get him back on track.

For now, it’s a C+ because this trade doesn’t move the needle in getting the Cubs closer to winning in the 2026 season.

Grade: C+

CubsSports