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...
Rangers Rotation Search May Be Zeroing In On A Needed Veteran Lefty
The Rangers have several holes to address this offseason, and the rotation remains one of the bigger ones after a year in which adding a reliable arm could help steady the group around the edges. Center field will draw plenty of attention, but the pitching side has a chance to shape how the front office spends, especially if it wants a starter who can bring some left-handed balance to the staff.
Trevor Rogers has emerged as a name worth watching as Texas weighs possible multi-year options. With a career 3.88 ERA and recent underlying performance that points toward a fit in the Rangers plans, he checks some of the boxes a team in need of rotation help would want. The question now is whether the Rangers decide his profile matches the type of veteran presence they want to build around this winter. [Read more 🡒]
Rangers Offseason Reset Starts With One Crucial Offensive Decision
The Rangers are heading into an offseason defined by accountability, and president of baseball operations Chris Young has already owned his part in a year that fell short. Texas finished with 80 wins, missed the playoffs for the third straight season and came up one game behind the Astros in the AL West, a frustrating finish for a roster that never quite found enough consistency at the plate. Young said changes are coming, and the coaching staff appears to be the first place the club will look for a reset.
Skip Schumaker is expected to be part of those conversations, and he acknowledged the coaching staff will be addressed soon. The most immediate focus is the lead hitting coach role, a reflection of how stagnant the offense looked over the course of the season. For a Rangers team that still believes it can contend in a tightly packed division, the next step is less about a wholesale teardown than finding the right voices to help the lineup take a real step forward. [Read more 🡒]
Rangers Offseason Just Got Complicated By Several Key Injury Decisions
As the Rangers closed out the 2026 season, Chris Youngs end-of-year injury update added a layer of uncertainty to what comes next. Several core players finished the year dealing with issues that ranged from bone spurs to fractures and strains, and the club now has a longer list than usual of medical check-ins to navigate before the offseason can really take shape.
Corey Seager and Ji-Hwan Bae were among the names tied to those injury questions, and some cases could still lead to surgery with recovery timelines stretching well beyond the final game. For a Rangers front office already weighing roster decisions for 2027, the health of players heading toward free agency could end up shaping more than just the winter medical report. [Read more 🡒]