Arizona Diamondbacks starting pitcher Jordan Montgomery has made a significant change in his representation after a surprising outcome in free agency. Montgomery, who had been expected to land a lucrative, long-term deal, has reportedly dropped his agent, Scott Boras, following a disappointing contract and has now signed with Joel Wolfe and Nick Chanock of Wasserman Sports & Entertainment.

Montgomery remained unsigned until the start of the 2023 MLB regular season, eventually agreeing to a one-year, $25 million contract with the Diamondbacks, which includes an option for another $25 million in 2025. This deal fell well short of the expectations surrounding Montgomery, with many, including ESPN’s Kiley McDaniel, projecting him to secure a contract in the range of five years and $106 million.

Montgomery wasn’t alone in his free agency struggles. He was one of four major clients of Boras who were left unsigned deep into the offseason. The other three—pitcher Blake Snell, outfielder Cody Bellinger, and third baseman Matt Chapman—also signed deals that were below initial projections. Snell eventually inked a two-year, $62 million deal with the San Francisco Giants, which included a player opt-out clause after 2024. Chapman signed a three-year, $54 million contract with the Giants, and Bellinger returned to the Chicago Cubs on a three-year, $80 million deal with two player opt-outs. While all of these deals were finalized in March, Montgomery’s situation stands out as the most disappointing, as he signed later and for only a one-year commitment.

Montgomery’s career began with the New York Yankees, where he spent parts of six seasons and posted a solid 3.94 ERA. However, his career trajectory took a notable upward turn after being traded to the St. Louis Cardinals and later to the Texas Rangers. In the 2023 season, split between the Cardinals and Rangers, Montgomery made 32 starts, going 10-11 with a career-best 3.20 ERA and 166 strikeouts over 188.2 innings. His performance in the playoffs was equally impressive, recording a 2.90 ERA in six outings, including five starts, which helped the Rangers secure a World Series title.

Given his standout performance on such a big stage, Montgomery was widely expected to command a significant contract in free agency. However, it appears that Boras may have overestimated the market, resulting in Montgomery’s underwhelming deal with Arizona. As a result, Montgomery has now turned to Wolfe and Chanock to represent him moving forward, likely seeking a better outcome in future negotiations.

Currently, Montgomery is working his way back into form in the minor leagues as he ramps up his pitch count in preparation for his Diamondbacks debut. Despite the disappointing contract, Montgomery has the potential to be a key contributor for an Arizona team that reached the World Series in 2023. However, the situation remains a letdown given the level of performance he delivered last season and what he might have expected to earn as a free agent.