Trade Deadline Outlook: Chicago Cubs

Led by All-Star starters Kyle Tucker and Pete Crow-Armstrong, the Cubs are in a great position to return to the playoffs for the first time since 2020.  Their position player mix could use some tweaks, but the team’s priority will be its battered rotation.

Jed Hoyer has had the top chair in the Cubs’ baseball operations department since Theo Epstein stepped down in November 2020.  Hoyer was the number two man in Epstein’s front office before that, after he’d led the Padres’ front office for two years.  He’s played a large part for “buy mode” contenders across many trade deadlines and has been unafraid to move prospects and good young players.  Hoyer sent a strong “all-in” message in December by trading last year’s first rounder Cam Smith along with three years of Isaac Paredes and five of Hayden Wesneski for one year of Kyle Tucker.

Hoyer is in the last year of a five-year contract with the Cubs, so it’s a bit odd to have him making long-term decisions for the franchise with his own future in doubt.  Back when Epstein stepped down, he said, “The organization faces many decisions this winter that carry long-term consequences; those types of decisions are best made by someone who will be here for a long period rather than for just one more year.”  Perhaps an extension for Hoyer is forthcoming.  For now, I’m sure, his focus is on shoring up the first-place Cubs for a deep playoff run.

Record: 54-36 (94.6% playoff probability)

Buy Mode

Potential needs: Two starting pitchers, starting third baseman, lefty-mashing first baseman, general relief help

With Jameson Taillon on the IL into August due to a calf strain, the Cubs’ rotation is down to two reliable established Major Leaguers: Shota Imanaga and Matthew Boyd.  Expected ace Justin Steele is out for the season due to Tommy John surgery.

Taillon still figures to be part of the playoff picture for the Cubs.  Colin Rea and Cade Horton are in the rotation at present, and Ben Brown made 14 starts before being optioned in late June.  Veteran Chris Flexen made 30 starts last year.  Jordan Wicks got the call four days ago but may be used in a long relief role.  Javier Assad, who started 29 games last year, has been dealing with an oblique injury all season.  It’s not clear what the Cubs will get from him in 2025.

There are enough rotation options on hand to get through the regular season, but the goal is to win the World Series.  Boyd, the Cubs’ All-Star lefty, is 34 years old and hasn’t shouldered a full workload since 2019.  This team needs to add two starting pitchers, including at least one who can start a playoff game.