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Breaking Down A Creative Hypothetical Cubs Trade For Former AL Cy Young Winner

Originally posted on Chicago Cubs on SI | By Nick Ziegler | Last updated Jul 30, 2025 9:30 PM ET

The Chicago Cubs are heading toward the trade deadline with a glaring need in the middle of a tight race with the Milwaukee Brewers for first place in the National League Central.

While it has been a fantastic season so far for the Cubs, they are by no means going to be able to coast in the second half of the year. Chicago is locked up in a tight division race with the Brewers, and the NL overall has been tough.

The Cubs have a chance to accomplish quite a bit this campaign, but they must improve their starting rotation to compete. While the duo of Shota Imanaga and Matthew Boyd is a good one, they are without Justin Steele for the rest of the season, leaving quite a void.

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Ideally, with an excellent lineup and strong bullpen, the team would be able to add a front-end caliber starter before the trade deadline.

There are a lot of potential options for the Cubs to think about, and they are fortunate to have a loaded farm system to be able to pursue many of those options.

Joel Reuter of Bleacher Report recently proposed a hypothetical trade that sent Cleveland Guardians pitcher Shane Bieber to the Cubs in exchange for Jonathon Long.

“He has yet to pitch at the MLB level this year as he continues his recovery from Tommy John surgery, but he is on the comeback trail, allowing four hits and one earned run with 14 strikeouts in 7.1 innings over his first three rehab starts,” Reuter wrote.

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This is certainly a creative idea for Chicago to potentially upgrade their starting rotation not only for the stretch run, but also in 2026 as well.

Bieber is recovering from Tommy John surgery and is currently working on his rehab assignment in the minors. With things going well, he figures to be ready soon to make his debut.

Before the injury, the 30-year-old was a former AL Cy Young award winner and could be a game-changer if he regains form quickly. This is a deal that would have some risk for Chicago, with pitchers reacting differently from coming back from the lengthy layoff. However, with him doing well in the minors it's an encouraging sign.

Furthermore, what makes the deal appealing is also the player option for 2026. With it likely he won’t pitch a ton, he could look to exercise that and prove himself fully in 2026, rather than testing the market right away.

Moving their fifth-ranked prospect would be a steep cost for the Cubs, but a healthy Bieber could be exactly what they are looking for.

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This article first appeared on Chicago Cubs on SI and was syndicated with permission.

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