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Trade Deadline Outlook: Chicago Cubs

By Tim Dierkes | July 8, 2025 at 1:52pm CDT

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.

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9 Comments

  1. Alan53

    5 hours ago

    Nothing too surprising here. My guess is that Hoyer won’t aim as high at the deadline as many suspect. I think he’ll concentrate mostly, perhaps exclusively, on relief pitching. The Cubs seem to think more in terms of “covering” innings than adding top starters, and Counsell seems to manage that way too.

    IMO they need more hitting–they have some pretty likely regression candidates come August-September–but I don’t think Hoyer agrees with me.

    I don’t think ONKC or any of the (somewhat dwindling) supply of top prospects are going anywhere.

    The Cubs went just over the CBT level last season, apparently by mistake, and unfortunately I think their top priority is to avoid going over again, and thereby facing steeper penalties. Yes, as the article points out, at the moment they have some payroll space to spare, but that would get used up very quickly if they traded for top rentals by July 31.

    1
    Reply
    • rondon

      4 hours ago

      I agree with most of this except I believe he will absolutely go after two starters. Aside from Taillon being out for the next month, Boyd and Horton are either at or close to the most innings they’ve ever pitched in a season. They’re gonna have to back off on both if they want them for the playoffs. And that can only happen with a couple more starters… Part of me almost wants them to let Shaw just play through it the way they let PCA do last season because he showed improvement at the plate. But they need a big RH bat so that’ll probly be addressed- as well as, hopefully, that anemic bench..

      2
      Reply
      • Unclemike1526

        3 hours ago

        They already have a RH bat they could easily swap out for Turner that can do more things than he can in Jonathon Long. All they have to do is DFA Turner and bring him up. What they need is a LH bat that can play a few positions That they haven’t been able to find for the last 3 years. And no they really don’t have one in the system except Ballesteros who only plays 2. C( Badly) and 1B( lamely).. As for needing 2 starters I don’t think they need any, But they’ll never give them a chance because they think their heads will explode or something if they brought them up. I’m not saying I wouldn’t add a starter if one fell into my lap, But the only way to get one is to let yourself get fleeced. And Alan totally underestimates Hoyer when he says top prospects won’t go anywhere. He’s already proven what he’ll do to keep his job with regards to the future.

        Reply
        • Alan53

          3 hours ago

          @uncle: I think you’ll get your wish when they bring up Birdsell in a few weeks. I think Brown will be back soon too. Wiggins seems to be hurt again.

          I am guessing Hoyer will NOT do what you are afraid he will: overpay for a mediocre SP. But we’ll know soon enough.

          Reply
        • Alan53

          3 hours ago

          @Uncle: Am I underestimating him, or overestimating him? I think you mean I am underestimating how stupid and reckless he can be with prospects. You are certainly right that there have been some ugly examples in the recent past.

          I think they see Alcantara as the kind of player to include in a trade, and that might happen if they find interest in him. But the rest of the better Cubs prospects are probably safe.

          1
          Reply
        • rondon

          3 hours ago

          Mike.. Ordinarily I’d agree but Long isn’t any more proven than Shaw is. Either are the pitchers in the system. And I don’t think Hoyer wants to risk them coming up and being Ben Brown 2.0 or not hitting any better than Shaw with the playoffs on the line. And I’m betting he wants one proven arm to go along with Shota and Boyd for postseason starts.

          1
          Reply
        • Unclemike1526

          2 hours ago

          There’s only one way to find out about Pitchers. Let them pitch in the Major Leagues against Major League hitters. Will there be growing pains? To be sure. But that’s the difference between having a POBO who is thinking of the future, or one that’s only concerned with saving his job. All his moves for this year scream he’s just trying to save his job when the team needs a guy who is playing the long game. They have a perfect chance to give some guys a look in pressure situations. And they won’t. How EXACTLY does one PROVE he can hit MLB pitching in Iowa? LOL

          Reply
        • Alan53

          1 hour ago

          @Uncle: I hope you are right that Hoyer is worried about his job. My take is even more pessimistic than yours: I think Ricketts has already decided to re-up him, and in fact the announcement could come soon. I think that if he makes bad trades–including trades of prospects–it will be because he’s stupid, not because he’s worried.

          Do you think there is any chance of a surprise trade of *major-league* talent, e.g., Shaw or Amaya? That feels unlikely to me, but I have read such speculation. And I have sensed for a while that Hoyer has mixed feelings about Amaya. (Or maybe I’m projecting, because I have mixed feelings about him.)

          1
          Reply
        • Unclemike1526

          2 mins ago

          I would rather he fired him but a least if he extended him he’d have to live with his decisions at this deadline. It might make him pause before he does any dumber than he has already. I’m not a Mike Rizzo fan either but I asked myself who would I rather have making the decisions at this trade deadline for the Cubs? Rizzo or Hoyer? And I decided hands down Rizzo over a guy who always gets fleeced it seems. As far as rumors go and the amount of people who have a blog or a podcast will throw stupid trade ideas around. You’re likely as not to hear anything about everybody. Somebody who’s trying to make a name for himself and a tiny bit of credit for picking the big mover at the deadline. In the old days when you just had newspapers you could trust stuff like that a little more. Now…… Anybody can say anything.

          Reply

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