Here’s the oddest Chicago Cubs trade idea of the offseason so far

The Chicago Cubs need pitching. They desperately need quality arms this coming season to replace a bevy of outgoing pitchers—like, their entire end-of-season starting rotation—for a shot at making a real postseason run in 2027.

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But they also need pitching beyond 2027. With Pete Crow-Armstrong hitting his prime and veterans like Alex Bregman and Dansby Swanson on the downside of their primes, there’s a limited window of opportunity for Chicago to make a realistic push for a championship.

The question, though, is how much can the front office add via free agency and how much can they grab via trade, given their current lack of farm system depth.

This means that if the Cubs are going to restock their pitching staff and put together a winning crew, they’re going to have to be aggressive and get creative.

Hunter Greene to the Cubs?

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One odd/interesting idea was recently floated out into the online cyberverse by Jordan Campbell of Cubbies Crib involving the Cubs, the Reds, and Reds ace Hunter Greene.

Specifically, Campbell talks of Chicago acquiring the former All-Star via trade as he recovers from his second Tommy John surgery.

Per Campbell:

“The Reds likely are begging for someone to take Hunter Greene and his money off their hands. It would seem that Greene misses the entire 2027 season while recovering from Tommy John surgery, so the trade compensation may not be as high as one would expect, especially if the Cubs are taking on most of the money owed. It’s a risk, but if Greene is healthy by 2028 (another big “if”), it could be the type damaged-goods move that Jed Hoyer loves.”

Make it make sense

The 27-year-old Greene had his surgery in August of this year and will definitely miss all of 2027—where he’ll earn $15 million. However, he’ll remain under team control through 2028 at $16 million and the Cubs would hold a $21 million club option on him for 2029.

On the surface, the Cubs making a trade for an injured pitcher recovering from his second Tommy John surgery in eight years—and paying him eight digits just to rehab and eight more digits on the hopes of a healthy return the following season—wouldn’t seem to make a lot of sense.

But Greene is an elite top-of-rotation starter when healthy and $56 million for two years of a healthy Greene is not a bad deal at all in today’s market.

The Cubs have already shown a willingness to acquire—and pay—an injured pitcher when they signed Shelby Miller, who had Tommy John surgery in the fall of 2025, to a two-year deal this past offseason with the understanding that a 2026 return wouldn’t be in the cards. But that was a $2.5 million deal on a bullpen arm, not a $31-$56 million gamble on a rotation piece.

Is this the type of gamble that the Cubs and Cubs President Jed Hoyer need to make as their organization works on building a stronger pitching infrastructure? Maybe.

If it worked out, the payoff would be great and the Cubs front office would look like geniuses. If it didn’t, though, heads could roll.

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