Arizona Diamondbacks starter Jordan Montgomery was developed as a pitcher by the New York Yankees. He made his MLB debut with them in 2017, became a valued member of the rotation, and stayed in the Bronx until 2022 when he was traded for center fielder Harrison Bader.
Montgomery had successful stints with the St. Louis Cardinals (3.11 ERA in 2022 and 3.42 in 2023, before he was flipped to the Texas Rangers) and was excellent with the 2023 World Series champions, contributing a 2.79 ERA in 67.2 frames in the regular season and starring in the playoffs.
He was in a prime position to cash in on free agency, but as he said so himself, his agent Scott Boras “kind of butchered it.” He continually asked for exorbitant contracts from teams and closed many doors for Montgomery, including one that would have seen him return to the Yankees.
Jordan Montgomery had a Yankees offer on the table in the offseason
In the end, he signed for the Snakes on a one-year, $25 million deal with a vesting option for 2025. He did so in late March, missing the entire spring training and ruining his preparation. As a result, Montgomery is currently a very expensive low-leverage reliever for Arizona, boasting a horrible 6.25 ERA.
“Jordan Montgomery complaining about his free agency when he’s making $25 million (and will make another $22.5M in 2025 once he declines his opt-out) and has a 6.25 ERA and negative 1.4 WAR is interesting,” Jon Heyman of the New York Post said. “Shouldn’t the Diamondbacks be the ones complaining? As for Montgomery recently telling the Boston Herald he would have been happy to sign with Boston, word is when the (Boston Red Sox) suggested a willingness to do a four-year deal, Montgomery never engaged with them…”
The “never engaged with them” part could have been because of the player, sure, but it has Boras written all over it. Do you know who else was open to a four-year deal? The Yankees.
“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,” the MLB insider wrote.
Boras drew criticism from many fans, specialists, and even people in the baseball industry for the way he managed free agency with specific players, and Montgomery was one of them. Yes, he is making $25 million in 2024, but could have signed a better, longer deal if it wasn’t for his agent.
