The Cardinals already showed this past offseason exactly the kind of move they like to make with a veteran starter.
They brought in Dustin May, got 21 starts out of him, and then turned him into another asset by sending him to the Milwaukee Brewers with JoJo Romero in exchange for No. 5 prospect Alexander Frias and No. 11 prospect Josiah Ragsdale. That blueprint could fit again this winter, and one name that makes a lot of sense is a familiar one: Jordan Montgomery.
Montgomery’s Cardinals run was tied to their last playoff team in 2022, when St. Louis picked him up from the New York Yankees.
A year later, during the 2023 fire sale, the Cardinals dealt him to the Texas Rangers. Montgomery went on to win a World Series that season, but the years after that were rough.
He signed late with the Arizona Diamondbacks before the 2024 season and posted the worst year of his career. Then came a lost 2025 season and most of the 2026 campaign missed as well.
He did at least get back on the mound in 2026, making 13 appearances out of the Rangers’ bullpen and putting up a 4.15 ERA. Now 33 and headed back into free agency, Montgomery looks like the kind of arm St.
Louis should strongly consider. The key development is simple: he’s healthy again.
That matters after the last few seasons, and it also changes the outlook on what he can offer a club that needs innings.
The Cardinals would also be betting on the version of Montgomery that was much more dependable before all the injuries and delays. From 2021 through 2023, he logged a 3.48 ERA in 94 starts.
If he gets a normal offseason this time - especially if he signs early - there’s reason to think he can get back closer to that level. And because of the recent struggles, the price should be manageable.
For St. Louis, that’s the appeal.
A deal in the neighborhood of the May trade, or even a little lighter because Montgomery is older, would fit a team that needs a veteran starter alongside a young roster. He’s been through October, he knows how to win, and he already has playoff experience with the Cardinals.
If the season goes sideways, the Cardinals could always follow the same playbook again and move him at the deadline. That’s why Montgomery should be near the top of their list once the market opens.
In Other News...
Jordan Walker Just Changed A Big Cardinals Decision
Jordan Walkers 2026 season gave the Cardinals exactly the kind of long-term answer they have been searching for. He put together a full workload, powered his way to 29 homers, swiped 22 bases and drove in 102 runs across 158 games, then added an All-Star nod and a Home Run Derby title to a year that firmly raised his profile in St. Louis. For a club trying to build around a young core, Walker only strengthened the sense that he belongs at the center of the conversation.
Even with the late-season dip, there is now a different kind of uncertainty around him, and it has less to do with whether he is part of the future than where the Cardinals fit him within it. Chaim Bloom confirmed Walker was playing through hip pain in September, a reminder that the final impression of the season came with some context attached. Walker and JJ Wetherholt are viewed as key pieces for what comes next, and the Cardinals suddenly have a big decision to make about how to handle that promising pairing. [Read more 🡒]
Cardinals Face An Offseason Decision That Could Box In Their Youth
The Cardinals enter the winter with a familiar kind of tension: a 77-85 finish, a young roster, and enough in-house talent to make the next step feel possible without a full reset. St. Louis has promising pieces already in the majors, along with high-upside names working their way up the farm system, including Jesus Baez and Rainiel Rodriguez, so any offseason shopping list has to account for both present need and future flexibility.
Bullpen help and a veteran starter make sense, and theres also a case for bringing in another option at third base. But thats where the organization has to be careful, because a heavy commitment there could crowd out the younger players the Cardinals are trying to develop. With so much of the roster still in the making, this winter may be less about solving everything at once and more about avoiding a move that blocks the very youth the club is counting on. [Read more 🡒]
Ivan Herrera Rescued Cardinals After A Game That Left Fans Fuming
For most of the night in Denver, the Cardinals had more to worry about than the Rockies. Doug Eddings drew plenty of ire for a series of disputed calls, including a safe ruling that went against St. Louis and a pitch clock violation that got manager Oli Marmol tossed. The frustration only grew when rookie Hancel Rincon was told to adjust his cap, a move Major League Baseball later acknowledged had gone too far and apologized to the pitcher for.
Ivan Herrera eventually gave the Cardinals something better to remember. With the game hanging in the balance, he launched a three-run homer in the ninth inning to turn a maddening night into a win, offering a sharp reminder that the lineup could still erase a whole lot of bad blood in one swing. Even after the final out, though, the conversation around this one lingered on the officiating and the ripple effects it left behind. [Read more 🡒]