Montgomery shows Scott Boras the door after lackluster Diamondbacks deal

The ex-Yankees pitcher, Jordan Montgomery
Amanda Paula
Thursday April 11, 2024

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Former New York Yankees pitcher, Jordan Montgomery, has made a significant change off the field, parting ways with his longtime agent, Scott Boras. This decision comes after Montgomery found himself settling for a contract that fell short of expectations during the recent offseason free agency frenzy.

Montgomery, previously represented by Boras, has now entrusted his career to Joel Wolfe and Nick Chanock of Wasserman, as reported by ESPN’s Kiley McDaniel. The move signals Montgomery’s dissatisfaction with the outcome of his contract negotiations under Boras’ guidance.

Montgomery’s free agency saga

The ex-Yankees pitcher, Jordan Montgomery and his former agent Scott Boras
AP

Despite a strong performance in the previous season, including a stint in the World Series, Montgomery found himself among four prominent Boras clients facing prolonged uncertainty in free agency. Alongside Blake Snell, Cody Bellinger, and Matt Chapman, Montgomery remained unsigned well into the offseason, a situation that puzzled many in the baseball world.

Ultimately, the ex-Yankee secured a one-year deal worth $25 million with the Arizona Diamondbacks just before the commencement of the season. However, this contract fell short of both his and industry expectations. McDaniel had initially projected a significantly more lucrative five-year, $106 million deal for Montgomery.

The disappointment surrounding Montgomery’s contract is exacerbated by the fact that it offers no long-term security, with only a one-year commitment from the Diamondbacks. Additionally, the deal includes a second-year player option that hinges on performance metrics, potentially limiting Montgomery’s earning potential.

Jordan Montgomery and the Yankees

The ex-Yankees pitcher, Jordan Montgomery
AP

Montgomery’s journey from the Yankees to the Diamondbacks follows a career trajectory marked by ups and downs. Drafted by the Yankees in 2014, he showcased promise before being traded to the St. Louis Cardinals in 2022. It was with the Cardinals and subsequently the Texas Rangers where Montgomery truly flourished, posting career-best numbers and contributing significantly to the Rangers’ World Series victory in 2023.

Notably, discussions had even arisen within the Yankees organization regarding the possibility of re-signing Montgomery before he ultimately opted for Arizona. Despite this interest, Montgomery pursued a fresh start with the Diamondbacks, signaling his readiness for a new chapter in his career.

Despite his on-field success, Montgomery’s off-field negotiations with Boras failed to yield the expected results. Now, as he prepares to make his debut with the Diamondbacks, Montgomery finds himself in a position of uncertainty, eager to prove his worth once again.

As Montgomery readies himself for the upcoming season, his situation serves as a reminder of the complexities and challenges inherent in professional sports negotiations. While his talent is undeniable, Montgomery’s experience highlights the importance of effective representation in navigating the intricacies of the baseball market.

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