If Major League Baseball’s spring free agency were likened to a game of musical chairs, it seems there’s only one chair left, but several teams vying for it. This presents a significant dilemma for the Yankees.
The remaining chair represents left-handed pitcher Jordan Montgomery, a former Yankee who is currently a free agent despite delivering outstanding performances during last year’s postseason and playing a pivotal role in the Rangers’ journey to win the 2023 World Series.
With their ace Gerrit Cole sidelined due to an elbow injury, the Yankees are now confronted with the decision of whether to actively pursue reinforcements for manager Aaron Boone’s now uncertain pitching rotation or to maintain their current stance. While there’s some positive news about Cole’s injury not requiring surgery and a projected return in early June, starting the season without another reliable starting pitcher would pose a significant risk for the team. This is where Montgomery becomes crucial – among the Yankees’ available options, he appears to be the last and best choice.
According to insights from New York Post insider Jon Heyman, there have been discussions between Montgomery and the Yankees. Heyman suggests that the Yankees initially leaned towards acquiring Blake Snell due to concerns from their analytics team about Montgomery’s pitching style, particularly his lack of high velocity and strikeout numbers. Additionally, rumors circulated that Montgomery may have preferred to sign with another team.
Nevertheless, with limited alternatives, the Yankees find themselves back in talks with Montgomery. While they had considered trading for Dylan Cease from the White Sox or signing Snell, those options didn’t materialize due to unwillingness to part with necessary assets or commit to significant financial obligations. The Rangers, too, filled a potential gap by signing Michael Lorenzen.
Montgomery remains available primarily due to financial considerations. The Yankees are hesitant to invest heavily in him, considering his previous stint with the team and his perceived value compared to other pitchers like Aaron Nola, who secured a lucrative contract with the Phillies.
Despite initial reservations, Montgomery has shown improvement since leaving New York, delivering solid performances for the Cardinals and Rangers in recent seasons, particularly during last year’s postseason.
While neither the Yankees nor Montgomery have shown overwhelming enthusiasm for a reunion, they may find themselves without better options. The fact that discussions are ongoing suggests both parties are at least open to the possibility.