ST. LOUIS – Less than two weeks away from the MLB trade deadline, teams in need of pitching will likely ask the St. Louis Cardinals about two pending free agents: Jack Flaherty and Jordan Montgomery.

After spending most of the season dead-last in the NL Central, the Cardinals are quietly playing some of their best baseball of the season. Having won five straight and eight of their last 10, the Cardinals now stand at 43-53 and might have a small window of opportunity to crawl back into the postseason race.


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The recent surge puts the team in a tough spot with Flaherty and Montgomery, both due for new contracts next season.

If the Cardinals are looking more ahead to future seasons, St. Louis could test the trade market and potentially pick up a haul for either starter. If contending this year is still the mindset, it would likely be in the Cardinals’ best interest to keep two steady rotation pieces rather than fill their spots midseason.

The Case For Trading

Flaherty and Montgomery have been strong in recent weeks for the Cardinals, so they could be in high demand for other contenders looking to bolster their depth around a potentially scarce market for proven arms.

Take away two blowup starts against the Angels and Giants, Flaherty is 7-3 with a 3.32 ERA with 90 strikeouts, showing traces of his top form from 2019. Montgomery is 3-0 with a 1.17 ERA and 28 strikeouts over the past month, averaging around six innings a game. The southpaw also has 11 quality starts this season, tied for 12th best in the majors.

Around the All-Star break, though before the recent surge, lead executive John Mozeliak suggested that trades and other changes would happen with the current roster with 2024 in mind. If building for next year is the end goal, moving Flaherty and/or Montgomery could net young assets in short-term and help the Cardinals find clearer paths for young arms, like Zack Thompson, Michael McGreevey and Gordon Graceffo, in the big picture. Plus, the team could try to bring back Flaherty or Montgomery in the offseason if the pitching prospects aren’t progressing as hoped.

The Case For Not Trading

Flaherty, Montgomery and Miles Mikolas frankly have really been the only somewhat reliable options in the Cardinals rotation to this point of the 2023 season. The Cardinals have built a knack recently as a team that catches fire in the second half, and it would be hard to envision that again without some stability in the starting rotation for the season’s final two months.

The veteran pitchers have taken advantage of their surroundings in recent weeks too, particularly the ground game. Though the Cardinals defense hasn’t been quite produced to the pedigree of a record-setting Gold Glove squad, the team’s 41 errors are third-fewest in the National League. Cleaner defense. Flaherty and Montgomery have built familiarity with the defense behind them that most other ready rotation options, internal and external, likely have not.

There could be some organizational benefits in keeping Flaherty and Mongtomery beyond this trade deadline as well. It could be easier to offer new contracts to either one if they finished their contract years in St. Louis. And even if neither are in the long-term plans, the Cardinals could extends a qualifying offer to both and receive a draft pick if Flaherty or Montgomery rejects a one-year deal and signs with another team next offseason.

As For Now

Flaherty is lined up for two at least two more starts before the deadline. In current order, those would be road matchups this Friday against the Chicago Cubs and next Wednesday against the Arizona Diamondbacks.

Montgomery is lined up for two at least two more starts before the deadline, both against the Cubs. In current order, he is expected to start Sunday’s series finale and one of next weekend’s games at home against the Cubs.

Bleacher Report and other publications have named Flaherty and Montgomery among the top players to watch ahead of the MLB trade deadline, which is 5 p.m. CT on Aug. 1, 2023.