The Cardinals Reunion That Makes Too Much Sense in Free Agency

The St. Louis Cardinals need a veteran hurler to pair with their young starting rotation.

Sep 19, 2026; Arlington, Texas, USA; Texas Rangers relief pitcher Jordan Montgomery (52) pitches against the Toronto Blue Jays during the fifth inning at Globe Life Field. Mandatory Credit: Jerome Miron-Imagn Images | IMAGN IMAGES via Reuters Connect

This past offseason, the St. Louis Cardinals wanted a veteran starting pitcher who could come in and help in the short term and then end up being an intriguing trade chip.

That's what happened with Dustin May. The righty came to town and made 21 starts before being traded to the Milwaukee Brewers, along with JoJo Romero, for No. 5 prospect Alexander Frias and No. 11 prospect Josiah Ragsdale. This offseason, the Cardinals could use another veteran hurler — whether they plan to sell pieces at the 2027 trade deadline or not. Someone who should be on their radar right now is actually someone who has been on the team before: Jordan Montgomery.

Montgomery was a member of the Cardinals' last playoff team in 2022. The Cardinals acquired him from the New York Yankees that summer. Then, in 2023, the Cardinals traded him to the Texas Rangers in a fire sale. Montgomery won a World Series with the Rangers that year, but everything since has been brutal. He waited a while to sign with the Arizona Diamondbacks before the 2024 season and then had the worst season of his career. Montgomery then missed the entire 2025 season and most of the 2026 campaign.

The Cardinals Should Look To Reunite

Aug 30, 2026; Milwaukee, Wisconsin, USA; Texas Rangers pitcher Jordan Montgomery (52) throws a pitch in the seventh inning against the Milwaukee Brewers at American Family Field. Mandatory Credit: Benny Sieu-Imagn Images | IMAGN IMAGES via Reuters Connect

In 2026, made 13 appearances out of the Rangers' bullpen and had a 4.15 ERA. Now, the big lefty is going to be a free agent again at 33 years old. The Cardinals should be in on him. He showed down the stretch that he's healthy. That's the important point right now because it wasn't the case over the last few years. Clearly, signing late didn't go well for him in 2024. When the market opens, the Cardinals should give him a call right away and try to get a deal done. He should have a full offseason ahead to prepare for the 2027 season.

Because of his troubles over the last few years, his price tag is likely going to be low. But this is also a guy who had a 3.48 ERA from 2021 through 2023 in 94 starts. He's finally healthy and can have a normal offseason, especially if he signs on the earlier side. He has the talent to return to that level of play. Offering something like the May deal — or even a bit less because he's older — would be a good move for a Cardinals club that needs a veteran hurler to pair with all of the young guys.

Montgomery knows how to win. He has won a World Series throughout his career and has pitched in a playoff game as a member of the Cardinals. St. Louis' roster is very young. Montgomery has the type of experience that could go a long way. Then, if the Cardinals struggle in the standings, flip him at the deadline like May. When the market opens, Montgomery should be a top target.