Yankees dream of reuniting with former starter suffers a rude jolt

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The New York Yankees were well placed to sign their former pitcher Jordan Montgomery following the desperation of the Diamondbacks, who demoted him to their bullpen just a few days ago. However, their dream suffered a jolt yesterday.

The former Yankees southpaw will undergo Tommy John surgery next week, casting doubt over his future and effectively ending his 2025 campaign before it could truly begin.

According to Nick Piecoro of the Arizona Republic, the 32-year-old Diamondbacks hurler is scheduled for the procedure after experiencing complications in his spring throwing program, initially attributed to an index finger injury. Montgomery made a brief spring appearance, tossing 2 2/3 scoreless innings, before evaluations revealed the more serious elbow condition.

A tough turn for Montgomery

Montgomery, who joined Arizona on a one-year, $25 million contract just days before the 2024 season commenced, endured significant struggles throughout last year. The deal, negotiated by agent Scott Boras, followed a prolonged free agency period during which Montgomery and fellow Boras clients misjudged market conditions, ultimately accepting short-term arrangements well below initial projections.

The 2024 season proved disappointing by every metric: Montgomery compiled an 8-7 record with a troubling 6.23 ERA, lost his rotation position to Ryne Nelson, and was relegated to bullpen duties before briefly reclaiming a starting role late in the season due to team injuries.

Despite these underwhelming results, Montgomery activated his $22.5 million player option to remain with the Diamondbacks for 2025. That decision now appears largely academic, as Tommy John’s reconstruction typically demands 12-15 months of rehabilitation, potentially sidelining him into the 2026 campaign.

A Yankees connection runs deep

Montgomery’s major league journey originated in New York, where the Yankees selected him in the fourth round of the 2014 MLB Draft. After debuting in 2017, he quickly established himself within the rotation. However, the Yankees traded him in August 2022 to the St. Louis Cardinals for outfielder Harrison Bader, a transaction that generated considerable debate among Bronx faithful.

Following a productive tenure in St. Louis, Montgomery was again traded—this time to the Texas Rangers at the 2023 deadline. He flourished in Texas, becoming an integral rotation component during their World Series championship run. He posted a 2.79 ERA across 11 regular-season starts and maintained a 2.90 ERA throughout six postseason appearances.

Those performances seemed to position him for lucrative free agency, but market hesitations—particularly regarding his long-term durability—likely contributed to the shorter agreement with Arizona.

Career at crossroads

Montgomery’s latest setback adds another chapter to his unpredictable career trajectory. While demonstrating periods of mid-rotation reliability, health concerns have persistently shadowed him. He previously underwent Tommy John surgery in 2018, shortly after his breakthrough season with the Yankees.

A second ulnar collateral ligament reconstruction—commonly termed revision Tommy John surgery—carries heightened risks and typically extends recovery timelines. Few pitchers regain their complete form following a second procedure, though exceptions like Nathan Eovaldi have demonstrated it remains possible.

Montgomery now navigates uncertainty both physically and contractually. While earning $22.5 million this season, unless the Diamondbacks offer a minor-league rehabilitation contract post-recovery, 2025 could represent his final guaranteed major league season.

Impact on Diamondbacks and broader MLB market

For Arizona, the timing proves especially problematic. Having lost significant rotation depth this offseason while counting on Montgomery’s resurgence, the organization must now scramble for alternative innings. Internal candidates, including Ryne Nelson, Tommy Henry, and Slade Cecconi, are expected to assume greater responsibilities.

More broadly, Montgomery’s situation highlights the volatility within baseball’s pitching market. His experience parallels other Boras clients in recent seasons, where inflated contract expectations and delayed signings have left players rushing to establish a rhythm—or in Montgomery’s case, secure stable health.

Yankees can only watch closely from afar

Though no longer wearing pinstripes, Montgomery’s injury reverberates in New York. The Yankees, already managing the season-ending absence of ace Gerrit Cole, continue monitoring pitching availability throughout the league. While no indications suggested an imminent Yankees-Montgomery reunion, the left-hander perpetually represented a potential mid-season contingency should he have entered the open market.

With Montgomery unavailable, the Yankees’ focus remains on internal development and potential trade targets, particularly if their injury challenges persist into the summer months.

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