The Chicago Cubs head into the offseason with a clear need: a frontline starting pitcher who can anchor the rotation and bring some swing-and-miss stuff to the top of the staff. And while the free agent market is flush with big-name arms, the Cubs’ front office under Jed Hoyer has consistently shown a preference for controlled talent via trade rather than writing massive checks in December. That brings us to Minnesota Twins right-hander Joe Ryan – a name that continues to surface as a logical trade target for Chicago.

Ryan checks a lot of boxes for a Cubs team looking to take the next step. He’s under team control through 2027, he’s coming off a strong season with a 3.42 ERA, and he struck out over 28% of the batters he faced – a number that jumps off the page in today’s game. He’s not just a solid mid-rotation arm; he’s a potential Game 1 starter in a playoff series, the kind of pitcher the Cubs lacked in 2025.

Now, we may have a better sense of what it would take to land him.

According to a recent mailbag discussion involving The Athletic’s Red Sox beat, Twins insider Dan Hayes reportedly suggested that Minnesota would be looking for two top-50 prospects in return for Ryan – one with a mid-range ceiling and another more of a developmental flier. That’s a relatively modest ask for a pitcher of Ryan’s caliber and contract status, especially in a market where controllable starting pitching is at a premium.

So what does that mean for the Cubs?

Chicago currently boasts three top-100 prospects: Owen Caissie, Moises Ballesteros, and Jaxon Wiggins. If we assume Caissie is off the table – a fair assumption given his offensive upside and the expected departure of Kyle Tucker – then Ballesteros becomes the likely centerpiece of any deal. The 20-year-old catcher has real offensive upside and could appeal to a Twins team that values versatile bats.

Wiggins, a hard-throwing right-hander with top-of-the-rotation potential, would be another obvious target for Minnesota. But the Cubs reportedly held him out of trade talks at the deadline, which suggests he may still be viewed as untouchable. If that’s the case, the Cubs would need to pivot.

That could mean putting Jefferson Rojas into the conversation. The young infielder has a high ceiling and has impressed with his approach at the plate. Pairing Rojas with a lower-level lottery ticket – maybe a high-upside arm from the complex leagues or a toolsy outfielder still a few years away – might be enough to get a deal done.

Another name to watch is Jordan Wicks. Once viewed as a potential mid-rotation mainstay, Wicks’ development has hit a few bumps, and the Cubs may be more willing to part ways with him now than they were a year ago. Including Wicks in a deal could help balance out the prospect package without touching the top-tier names like Caissie or Wiggins.

Make no mistake – trading for Joe Ryan won’t come cheap. But it’s the kind of move that signals intent.

The Cubs are no longer in a rebuild. They’re in the business of winning, and acquiring a pitcher like Ryan – someone who can lead a rotation and still has multiple years of control – is exactly the type of calculated gamble that can pay off big in October.

It’s also worth noting that while the price might sting – and it likely will be higher than what the Cubs gave up in the Kyle Tucker deal – the long-term value of a controllable arm like Ryan can’t be overstated. You’re not just renting him for a playoff push. You’re adding a key piece to a rotation that could carry the franchise for the next two seasons and beyond.

The Cubs have the prospect capital to get this done. Now it’s just a matter of how bold they’re willing to be.