8 offseason targets for Chaim Bloom to shore up the Cardinals rotation

Jordan Montgomery

Oh look! A former Cardinal! While this isn't John Mozeliak's show to run anymore, I do think former Cardinals are still likelier candidates to return than you would think, and Montgomery is probably the highest upside play of any potential Cardinal that the club realistically reacquires this offseason (sorry, Zac Gallen hopefuls. That's not happening).

After being traded from the New York Yankees to the Cardinals for Harrison Bader at the 2022 trade deadline, Montgomery put together an excellent 32-start stretch with St. Louis over the next 365 days, posting a 3.31 ERA and 3.50 FIP in 184.2 innings of work. Montgomery was especially great during the summer of 2023, prompting the Texas Rangers to make a deadline move for him, and Montgomery helped lead Texas to a World Series title.

In free agency, Montgomery's agent, Scott Boras, overplayed his hand and cost Montgomery a long-term extension, forcing the lefty to take a two-year deal with the Arizona Diamondbacks super late in the game. Montgomery definitely felt like that negatively impacted his performance in 2024, where he posted a 6.23 ERA in 21 starts and four relief appearances.

Unfortunately for Montgomery, he then tore his UCL in spring training this past year and had Tommy John surgery. Because of this, Montgomery may not even pitch until May or June of 2026, which makes his fit with the Cardinals a lot more awkward if we are being honest.

At the 2025 trade deadline, the Milwaukee Brewers acquired Montgomery from the Diamondbacks in order not to give up a prospect for reliever Shelby Miller, so Montgomery finished his rehab as a part of the Brewers this year.

On one hand, this is for sure a buy-low opportunity for Bloom, but actually probably works more so as a midseason reinforcement and potential option for 2027 than an arm that the club can use as depth early in the season. But as well know, pitching injuries are unpredictable, so maybe having a guy like Montgomery coming back midseason would be a welcome addition when the time came.

I could easily see Montgomery latching on with an organization like the Brewers, though, or a different team that is in contention, but if he wants to rebuild his value to his free agency again in a healthy spot eventually, then looking to an organization with opportunities like the Cardinals may be in his best interest.