Former Yankees pitcher Jordan Montgomery did not have a “butchered” offseason on its own. It was rather his doing that undid his winter negotiations.
As his career with the Diamondbacks falls to match expectations, Montgomery has suggested that his arrival in Arizona was a result of missteps by his former agent, Scott Boras.
However, Jon Heyman of The New York Post reveals an interesting side. According to him, Montgomery declined a deferred four-year, $72 million offer from the Yankees. Heyman suggested that the ex-Yankees pitcher might have secured a more lucrative deal with the Boston Red Sox in retrospect.
“Montgomery also turned down a four-year deferred Yankees offer for $72M, and Arizona’s deal was probably better. But in hindsight, he very likely could have gotten bigger bucks in Boston. …,” he wrote.
According to Heyman, Montgomery also engaged with the Red Sox, participating in a lengthy Zoom meeting. However, he did not pursue negotiations further when Boston proposed a four-year contract. This decision was reportedly influenced by Montgomery’s doubts about the team’s playoff prospects and his desire to return to the Texas Rangers.
In a conversation with The Boston Herald, Montgomery confirmed the meeting with Boston but minimized its importance, expressing disappointment with Boras’ handling of negotiations. Following the episode, he split from Boras and signed with Wasserman for representation.
The connection between Montgomery and Boston seemed natural, especially given the Red Sox’s need for starting pitching and his wife completing a medical residency in the city.
The Red Sox, per Heyman, made a strong push for Montgomery, including a three-hour Zoom meeting where they outlined how he could strengthen their rotation. Despite their efforts, the former Yankee opted to explore other opportunities.
Despite this, Montgomery claimed Boston never presented a formal offer, though Heyman previously reported that Boston had put forth a multi-year deal. He, however, reportedly had his sights set on a reunion with the Rangers, with whom he won the World Series.
Montgomery fails to revive career in 2024
In the end, Montgomery signed a two-year, $47.5 million contract with the Diamondbacks in late March. His tenure in Arizona has been rocky, with a 6.25 ERA, 1.64 WHIP, and 73 strikeouts over 108 innings. Struggling in the starting rotation, Montgomery was moved to the bullpen after his last start on Aug. 21. In four relief appearances since he has given up seven earned runs in 13 innings.
Montgomery played a crucial role in the Rangers’ 2023 World Series victory and was hoping to re-sign with the team. When the desired offer from Texas didn’t materialize, he opted for a one-year, $25 million contract with the Arizona Diamondbacks, which includes a $22.5 million player option for 2025.
His performance with the Diamondbacks has been disappointing, as he has posted a 6.25 ERA over 108 innings. His struggles led to a relegation to the bullpen in late August after maintaining a 6.44 ERA in his first 19 starts.
The left-hander spent the initial five and a half seasons of his MLB career with the Yankees, where he recorded a respectable 3.94 ERA across 97 starts. In a surprising move, he was traded to the St. Louis Cardinals at the 2022 trade deadline for center fielder Harrison Bader.
Montgomery’s tenure with the Cardinals was successful, as he achieved a 3.31 ERA in 32 starts. He was then traded to the Rangers at the 2023 deadline, where he played a vital role in securing the franchise’s first World Series title. During the postseason, he went 3-1 with a 2.90 ERA in five starts and one relief appearance.
In hindsight, the Yankees’ decision not to re-sign Montgomery appears to have been beneficial, given his current struggles. This decision also created an opportunity for young pitcher Luis Gil to secure a spot in the rotation and emerge as a contender for the AL Rookie of the Year award.
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