5 most likely Jordan Montgomery destinations after Yoshinobu Yamamoto signing

Where will one of the top free agent pitchers land?

Jordan Montgomery
Jordan Montgomery / Richard Rodriguez/GettyImages
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The New York Yankees are a possible destination for Montgomery

While the Yankees always appear stacked in the way of starting pitching, the club may seek to reunite with the lefty they drafted in 2014 from the University of South Carolina.

Gerrit Cole, Carlos Rodon, and Nestor Cortes are the Yankees' top options in their rotation. The rest of the rotation includes Clarke Schmidt, Yoendrys Gomez, Clayton Beeter and Luis Gil. These are certainly young and talented arms, but are not the veteran depth the club desperately needs with Rodon and Cortes each having issues staying off the injured list.

While Montgomery is a fan of the beard he has grown since leaving the Yankees, he could shave if it meant returning to the club that drafted him. The Yankees can give Montgomery what he has earned in the way of a big contract.

The St. Louis Cardinals are a possible destination for Montgomery

Cardinals fans would feel relieved if Cardinals president of baseball operations John Mozeliak added one more starting pitcher to the three he has already added this offseason. Mozeliak promised fans to add "pitching, pitching, pitching" after the worst season Cardinals fans have seen in decades.

Pitching was a glaring need addressed in 2023 when it was ultimately too late to help with the season. Paul DeJong, Jordan Montgomery, Jack Flaherty, and Jordan Hicks were all dealt for several prospects that will bolster the club's roster in the coming years.

This offseason, starting pitching was addressed with the acquisitions of Sonny Gray, Lance Lynn, and Kyle Gibson. While these are fine additions when paired with Miles Mikolas, Steven Matz, and several young options that include Zach Thompson and Matthew Liberatore, more is needed. The Cardinals could benefit from another healthy, veteran arm.

Bringing back Montgomery would be ideal for the Cardinals. While it is not clear if the Cardinals would be open to offering up the payday Montgomery has earned, it is something they must consider to improve a pitching staff that had a disastrous 2023.