Chicago Cubs linked to risky Cy Young free agent gamble

The Chicago Cubs face a potentially overwhelming task this offseason. Aside from having to work around the pending free agency of corner outfielders Seiya Suzuki and Ian Happ, as well as catcher Carson Kelly, they’ll also have to pretty much rebuild their entire starting rotation.

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Matthew Boyd is expected to turn down his part of the $15 million 2027 mutual option with Chicago. Clay Holmes is expected to walk away from his $12 million player option as well. Meanwhile, Kevin Gausman, Shota Imanaga, and David Peterson will all become unrestricted free agents.

For those keeping track, that’s the entire 2026 end-of-season Cubs starting rotation potentially walking away this offseason.

Doubts and questions ahead of 2027

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The starting pitching left behind is full of question marks. Justin Steele hasn’t pitched in nearly two full seasons due to elbow surgery in early 2025 and a subsequent setback in his recovery this past season. Cade Horton will miss most—if not all—of 2027 recovering from Tommy John surgery in April. Edward Cabrera, meanwhile, suffered through a debut season with the Cubs full of injury and disappointing inconsistency. Swingman Javier Assad has been solid, but is unlikely to advance beyond a fourth or fifth starter role.

With nobody major league-ready in the farm system, Chicago will have to take a deep dive into the free agent talent pool if they want to make a serious run at the postseason this coming year and in the immediate future beyond that.

Although they’ll have plenty of money coming off the books to facilitate some big free agent buys, there will also be some rolling-of-the-dice gambles that need to be taken.

Shane Bieber to the Cubs?

One of those potential free agent gambles—former Cy Young Award winner Shane Bieber—was recently mentioned by Victor William of Blue Jays Insider:

“Shane Bieber won’t lack suitors if he leaves the Blue Jays. The Cubs, Braves and Orioles all have the rotation holes to make a run at him.

The 31-year-old is projected by Spotrac to land a one-year, $13.1 million deal. That’s a prove-it contract after a 2026 in which he posted a 4.37 ERA, his highest since his 2018 rookie year.

The Cubs look like the most aggressive threat. Shota Imanaga, Aaron Civale and Kevin Gausman are all pending free agents, leaving their rotation thin.”

Bieber’s history of injury is long and troubling. He had Tommy John surgery in April of 2024 and has only managed to pitch 18 big league innings since then as he went through recovery and a 2026 full of setbacks.

He’s hitting the free agent market with a lot of questions hanging over his head and, because of that, a very affordable asking price on, likely, a one-year contract. Given his recent injury history, the Spotrac $13.1 million valuation may be a lot higher than the number he actually gets.

When healthy, there’s no doubting what the two-time All-Star can bring to a rotation. He’s a true ace with elite control and a genius-level pitching IQ. The problem, of course, is that he hasn’t been healthy for a good long while.

But on a comparatively cheap one-year contract, the risk-reward potential might be too good to pass up for the pitching-desperate Cubs.

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