Arizona Diamondbacks pitcher Jordan Montgomery recently opened up about his experiences during last year’s free agency period, expressing disappointment over how his negotiations were handled by former agent Scott Boras. Montgomery, like many of Boras’ clients, held out for a lucrative, long-term contract throughout much of the offseason but ultimately settled for a shorter deal with Arizona.
In an interview with Mac Cerullo of The Boston Herald, the 31-year-old left-hander didn’t shy away from criticizing Boras’s approach during the process.
“Obviously, Boras kind of butchered it, so I’m just trying to move on from the offseason and try to forget it,” Montgomery candidly stated.
Montgomery secured a one-year contract with the Diamondbacks that includes a player option for the 2025 season, earning him $25 million this year with the potential for the same salary if he opts in for the following year. Despite the financial security, Montgomery had hoped for a longer-term commitment that reflected his performance and contributions on the mound.
This season has proven challenging for Montgomery, as he has struggled to find consistency on the field. Over 19 starts, he has posted a 6.44 ERA with 67 strikeouts across 95 innings pitched, resulting in a -1.5 WAR—the lowest of his Major League Baseball career. These struggles have undoubtedly impacted his market value and could influence his decision to test free agency again or exercise his player option for 2025.
In response to the disappointing outcome of his free agency and subsequent performance issues, Montgomery made a significant change by parting ways with Scott Boras in April. He has since enlisted the representation of Joel Wolfe and Nick Chanock from the Wasserman Group, hoping that the new partnership will better align with his career goals and negotiating strategy moving forward.
Reflecting on the past year, Montgomery’s frustration is evident, especially considering his successful 2023 season with the Texas Rangers, where he played a pivotal role in their World Series championship run while maintaining an impressive 3.20 ERA over 32 starts. Missing the opportunity to capitalize on that success during free agency has been a tough pill to swallow.
As Montgomery looks ahead, his focus remains on improving his performance and regaining his form on the mound. A strong finish to the current season could reinvigorate his value and present new opportunities, whether through exercising his player option or exploring free agency with a fresh perspective and representation.
The situation underscores the high-stakes and often unpredictable nature of MLB free agency, where negotiations and representation can significantly impact a player’s career trajectory. Montgomery’s experience serves as a reminder of the importance of alignment and trust between athletes and their agents in navigating the complex landscape of professional sports contracts.
