Feb 26, 2021; Jupiter, Florida, USA; A general view of the St. Louis Cardinals logo on the stadium at Roger Dean Stadium during spring training workouts. Mandatory Credit: Jasen Vinlove-Imagn Images Jasen Vinlove-Imagn Images

Cardinals Free Agent Reunion Makes Almost Too Much Sense

Originally posted on St. Louis Cardinals on SI
By Patrick McAvoy | Last updated Oct 2, 2025 11:00 AM ET

It sounds like the St. Louis Cardinals will pursue some starting pitching help this offseason.

Derrick Goold of the St. Louis Post-Dispatch shared that the Cardinals will look to add at least one starting pitcher this offseason under Chaim Bloom.

"For example, Bloom said he’ll go shopping for players. This previous offseason, as the Cardinals sought to trim payroll and begin the transition to Bloom’s leadership, they did not sign a free agent to a major league contract until spring training. Bloom said he plans to look into the free-agent market to fill a need in the rotation, add a veteran reliever for the bullpen and possibly add depth. Chairman Bill DeWitt Jr. and Bloom have not talked payroll budget yet — that will be set in part by the financial picture the Cardinals have at the end of next month."

In response, FanSided's Josh Jacobs floated eight potential fits to help in this area. One that stood out was old friend Jordan Montgomery.

St. Louis will look to add

Benny Sieu-Imagn Images

"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)," Jacobs said. "...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."

Montgomery is going to be available this winner after a rough two seasons. He struggled with the Arizona Diamondbacks in 2024 and then was hurt all year this year. He's going to need to rebuild his value and he's already has success in St. Louis. Adding him at this point isn't likely to be expensive, but he would give the club a high-end starter if he can return to form. A great idea.

This article first appeared on St. Louis Cardinals on SI and was syndicated with permission.

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