The Cubs have already shown how far they’re willing to push to land Reid Detmers, and that makes this winter feel like a continuation of the same chase rather than a fresh start. At the trade deadline, Chicago got close enough on the Los Angeles Angels left-hander that a deal seemed within reach before it fell apart at the last moment. That miss sent the Cubs to Ryan Zeferjahn instead, but it didn’t do much to hide how strong Jed Hoyer’s interest was in Detmers.
That’s why it would be a mistake to write Chicago out of the conversation once the market opens again. The Cubs have been here before with pitchers they covet.
They spent years circling Edward Cabrera and Jesús Luzardo before finally landing on an Owen Caissie-led package that got Miami to agree. Even before Cabrera was actually acquired in January 2026, the Cubs had treated him as their “top target” at the 2025 trade deadline.
So the pattern is familiar. The front office may have had other priorities this summer with Kevin Gausman, Clay Holmes, and Zeferjahn all coming into the fold, but Detmers was clearly near the top of the wish list.
That pursuit does not feel finished. If anything, it looks like the early stages of a longer process.
The catch is that Chicago will have to pay up, and the deadline activity already trimmed away several of its best trade chips. Jefferson Rojas went to Cleveland in the Holmes deal, Brett Bateman was sent to Toronto for Gausman, Jonathon Long joined Caissie in Miami for Braxton Garrett, and Moises Ballesteros and Mason McGwire were both part of the Zeferjahn trade.
That doesn’t mean the Cubs are out of ammo. It does mean a Detmers deal gets trickier if they want to avoid stripping the farm system bare.
There’s another wrinkle, too: by bringing in Zeferjahn, Chicago already used two prospects the Angels valued highly. This conversation may not be starting from scratch, but it also won’t resume as if the parties are just picking up from the one-yard line.
Detmers himself is a big reason the price keeps climbing. He’s 27 and one of the best controllable starters available.
His overall line - a 3.36 ERA, 3.01 FIP, 28.5% strikeout rate, and 4.9 fWAR - is strong enough on its own, and his second half gives interested teams even more reason to chase him. Over 76⅓ innings after the break, he posted a 1.89 ERA and a 2.54 FIP.
That kind of performance raises the cost, but it also explains the appeal. The Cubs may still be working through the wreckage of their failed Cabrera pursuit, but that shouldn’t stop them from taking another big swing this offseason.
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