I’ve been closely observing Jed Hoyer for a very long time, and one consistent trait in his leadership style is his patience. Throughout his career, Hoyer has been known for waiting until the very last possible moment to make key decisions — whether it’s arbitration filings, tender deadlines, Rule 5 choices, free agency moves, or trades involving the Cubs.
He typically delays action as long as he can, operating under the belief that while moving early might offer some upside, waiting allows for the collection of more information — often crucial — to make a better-informed choice. I don’t always agree with that method, but the rationale is clear.
However, that approach might be shifting.In a recent interview with 670 The Score, Hoyer spoke about the approaching trade market and, in a notable change of tone, expressed a stronger desire than usual to strike a deal as soon as it’s realistically feasible.
“If deals are there or transactions are there, certainly, I mean, every turn through the rotation or every outing you get extra out of a player adds value. So, it makes a lot of sense. When we were on the sell side, we were very aware of that.
“Sometimes some of the sellers haven’t declared themselves (early), so if it was a cold year for sellers, it made sense to kind of jump the market rather than wait for the market to get flooded as you got close to the deadline. We were pretty aware of that as a seller. I think as a buyer, certainly, it makes sense. If the prices aren’t prohibitive, it makes sense to make an earlier deal rather than a later deal.”
Of course, the big caveat here is “if the prices aren’t too steep,” which is often the case early in the market. Still, this represents a noticeable shift from Hoyer’s typical approach. It also aligns with a report from exactly two weeks ago, when Bruce Levine indicated that the Cubs might look to acquire a starting pitcher before the end of June.
Jameson Taillon and Matthew Boyd are currently leading the rotation, with Colin Rea holding things down reliably at the back end. But with Justin Steele out for the season and uncertainty surrounding what, if anything, the Cubs can count on from Javier Assad, the need for rotation help is pressing.
Cade Horton has been impressive, but he’s already thrown nearly double the innings he did last year (65.1 compared to 34.1), and Ben Brown has been far too inconsistent — mixing solid outings with complete meltdowns — to be a dependable option moving forward. Even with Shota Imanaga returning and the Cubs possibly avoiding strict innings limits, the need for a starter right now is just as crucial as finding one for a potential playoff run.
So, if a team is open to dealing a starting pitcher well before the deadline — likely more of a depth piece than a playoff ace — Jed Hoyer seems more inclined than usual to act early. And that might be a smart move.
Plus, if a club is open to parting with a high-end, front-line starter, it helps that one of the Cubs’ top trade assets is absolutely tearing it up in Triple-A right now.
Owen Caissie did not have a great start to his 2025 season. And whether that bothered you because of his potential as a future Cubs outfielder … or as an immediate Cubs trade chip … it was a problem. But in early-to-mid-May, he turned his season around on a DIME. And one way or another, that’s a VERY good thing for Jed Hoyer’s front office and the Chicago Cubs, who will be looking for upgrades at the 2025 MLB Trade Deadline with Caissie as an increasingly valuable chip.
… In fact, given his status as a top-100 prospect, his proximity to the majors, his improved performance, and the fact that the Cubs have four outfielders ahead of him on the depth chart right now, Caissie is probably the most valuable and most likely chip to be dealt. And the better he plays now, the more Jed Hoyer will be able to get for him.
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