In light of Jordan Montgomery’s surprising demotion to the bullpen by the Arizona Diamondbacks, speculation is swirling about a potential reunion with the New York Yankees. The left-hander, who spent his formative MLB years in pinstripes from 2017 to 2022 before being dealt to the Cardinals, now finds himself at a career crossroads. His desperate yet bumpy stretch in Arizona has opened the door for a possible trade — and the Yankees might be listening.
Arizona sports radio personality John Gambadoro recently noted that several clubs have shown interest in Montgomery. While the suitors haven’t been publicly named, the Yankees, grappling with rotation depth issues, would be a logical landing spot.
Diamondbacks’ Montgomery desperation
After playing a key role in the Texas Rangers’ 2023 championship run, expectations were high for Montgomery entering free agency. But a drawn-out offseason negotiation meant he didn’t land a deal until late March 2024, when the Diamondbacks signed him to a one-year, $25 million contract with a vesting option for 2025.
By skipping all of spring training, Montgomery entered the season unprepared, and the results showed. In 21 starts, he registered a disappointing 6.23 ERA before being shifted to a bullpen role in August. Diamondbacks owner Ken Kendrick didn’t mince words, calling the signing a “horrible decision” and personally taking the blame. Despite the setback, Montgomery exercised his $22.5 million player option for the 2025 season, ensuring he’ll remain in Arizona unless moved.
The D-backs, for their part, haven’t been shy about exploring trade options. General manager Mike Hazen confirmed last week that the club has fielded calls about Montgomery as part of a broader evaluation of its rotation. According to insiders, Arizona has asked at least one team to take on $13 million of his salary — an ask that reflects their lingering belief in Montgomery’s upside.
Yankees’ rotation woes and advantage of a familiar face
The Yankees’ pitching depth has taken a major hit with Gerrit Cole sidelined following elbow surgery. With the reigning AL Cy Young winner likely out for the entire 2025 season, GM Brian Cashman has acknowledged the difficulty of replacing such a crucial arm, though he stopped short of promising any blockbuster trades. Still, he made clear the club remains open to opportunities to strengthen the rotation.
Montgomery, meanwhile, is attempting to turn the corner. In a recent Cactus League appearance against the Rockies, he showed signs of regaining form. He delivered 2.2 scoreless innings, allowed three weak-contact hits, struck out two, and issued a leadoff walk. His sinker averaged 90.3 mph — still 1.5 mph below his 2024 average but trending up since his spring debut. It’s worth noting he began camp behind schedule due to a finger strain, putting him a step behind the rest of Arizona’s starters.
Pros and cons of a Bronx reunion
Bringing Montgomery back to New York comes with both promise and potential pitfalls. On the positive side, he knows the Yankees‘ clubhouse culture and has previously thrived under pressure in the Bronx. Given the current uncertainty in the rotation, his experience and left-handed presence could provide needed stability.
On the flip side, Montgomery’s recent performance and hefty salary present clear concerns. A 6.23 ERA isn’t easily ignored, and incorporating a $22.5 million commitment into an already top-heavy payroll would require financial gymnastics — especially with luxury tax implications in play.
That said, there’s flexibility on Arizona’s end. Reports indicate the Diamondbacks might be open to eating up to half of Montgomery’s salary in a trade and even packaging a lower-tier prospect to make a deal more attractive. For the Yankees, this could represent a relatively low-risk move. Absorbing some salary in exchange for a serviceable starter and a young asset might be a palatable trade-off — particularly if Montgomery can bounce back to his 2023 form.
Weighing the market and other paths
With multiple teams reportedly showing interest in Montgomery, the Yankees won’t be alone if they choose to pursue a deal. Arizona’s willingness to subsidize part of his contract could create a competitive bidding situation, forcing interested clubs to move quickly.
If the Yankees decide to look elsewhere, options remain. Pitchers like Erick Fedde or revisiting talks around Dylan Cease could provide similar rotation depth with different financial and performance profiles. These alternatives may come with their own set of risks, but they also offer the chance to diversify the rotation without the baggage of a rebound project.
The future ahead
Trading for Jordan Montgomery isn’t a simple plug-and-play decision for the Yankees. It’s a balancing act — weighing the urgency of the current pitching crisis against the financial and performance risks tied to the left-hander. A reunion could provide a steady hand and a familiar face, but only if the front office believes in Montgomery’s ability to rebound.
As Opening Day approaches and the Yankees brace for a season without their ace, this situation deserves close attention. If the price — both in dollars and talent — is right, Montgomery might just be the bridge New York needs to weather the storm.
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