The Yankees continue to scan the trade market for additional starting pitching as they look for ways to bolster their rotation in the wake of Gerrit Cole’s injury.
According to Joel Sherman of the New York Post, the Yankees have reached out to both the San Diego Padres about Dylan Cease and the Miami Marlins regarding Sandy Alcantara. Both pitchers would bring ace-level talent, but the cost in prospects remains a major hurdle.
Yankees Considering a Reunion With Jordan Montgomery?
Sherman also floated the idea that the Yankees could target a familiar face—Jordan Montgomery.
The left-hander is entering the final year of a two-year, $47.5 million contract with the Arizona Diamondbacks. He’s set to earn $23.75 million in 2025, but Diamondbacks owner Ken Kendrick recently admitted that he regretted signing the deal. That has sparked speculation that Arizona could look to shed some of his salary via trade.
Montgomery’s 2024 season was rough. After helping the Texas Rangers win the 2023 World Series with a stellar 3.20 ERA, he struggled last year, posting a 6.23 ERA over just 117 innings. Injuries played a role in his decline, and now he’s working his way back, throwing 40 pitches over a simulated two-inning session last weekend.
If the Diamondbacks are willing to eat a chunk of his salary, the Yankees might consider rolling the dice on a bounce-back season. But given their rotation already features two left-handers in Max Fried and Carlos Rodón, adding another southpaw who comes with major question marks might not be the best use of their resources.
A High-Risk, High-Reward Gamble
Montgomery has a history with the Yankees, but this version of him is a far cry from the one they traded away in 2022. Betting on a pitcher coming off an injury-plagued season is always a gamble, and with Carlos Carrasco already expected to be in the rotation to start the season, adding another uncertain piece could backfire.
If the Yankees do pull off a trade for pitching help, it’s far more likely they pursue a proven, durable arm like Cease rather than take a chance on Montgomery.