Cubs Rumors: Jack Flaherty could be open to a Cody Bellinger-type free agent deal

Unlike many of the other top free agent starting pitchers available this winter, Jack Flaherty headed into the offseason unburdened by a qualifying offer. That fact, alone, made it likelier the Chicago Cubs would take a run at him, as opposed to other top-tier starters like Max Fried or Corbin Burnes.

Now, according to The Athletic (subscription required), Flaherty may wind up settling for a shorter-term, high-AAV deal with opt-outs - which could prompt Jed Hoyer and the Cubs to circle back on the right-hander, even after adding the likes of Matthew Boyd and Colin Rea to the rotation mix.

Flaherty, 29, is coming off his best season in years, split between the Detroit Tigers and Los Angeles Dodgers. All-in, the former first-round pick made 28 starts, throwing 162 innings and working to a 3.17 ERA/3.47 FIP in 2024. He struggled in October, allowing 18 earned runs in 22 frames, but the big takeaway from his season was clear: he looked healthy and ready to anchor a rotation again.

If the idea of a short-term contract with opt-outs sounds familiar, it's because it's the same path the Cubs took with Cody Bellinger last offseason. After being cut by the Dodgers, Bellinger desperately needed to prove he still had something to offer - and a one-year pillow deal with Chicago allowed him to do just that. He turned in a bounceback 2023 that led to his being named National League Comeback Player of the Year - but even so, didn't fare well on the open market and eventually returned to the Cubs on a three-year, $90 million deal with opt-outs after 2025 and 2026.

Flaherty may be facing a similar skepticism, despite his solid results in 2024. After all, from 2020 to 2023, we're talking about a guy who pitched more like a back-end starter than an ace (4.42 ERA, 94 ERA+, 1.398 WHIP) who battled numerous injuries during that stretch. A long-term investment after one bounceback season isn't an idea most front offices are going to jump at.

If Flaherty is, indeed, open to such a pact, the Cubs have to jump. They are yet to seriously re-invest the Bellinger savings after they traded him to the Yankees and a rotation with Flaherty penciled in alongside Justin Steele and Shota Imanaga would give Chicago a formidable trio, especially thinking ahead to potential postseason matchups.