The Yankees offered the former left-hander $72 million, but he declined

Arizona Diamondbacks starting pitcher Jordan Montgomery was drafted by the New York Yankees. He made his MLB debut with them in 2017, became a valued member of the rotation and remained 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 being traded to the Texas Rangers) and was excellent with the 2023 World Series champions, contributing a 2.79 ERA in 67.2 innings in the regular season and starring in the playoffs.

He was in a perfect position to take advantage of free agency, but as he himself put it, his agent Scott Boras “kind of blew it.” He continually demanded exorbitant contracts from teams and closed many doors for Montgomery, including one that would have seen him return to the Yankees.

Jordan Montgomery had an offer on the table from the Yankees during the offseason

He eventually signed with the Snakes on a one-year, $25 million deal with a vesting option for 2025. He did so in late March, missing all of spring training and ruining his preparation. As a result, Montgomery is currently a very expensive, low-leverage reliever for Arizona, with a horrible 6.25 ERA.

“Jordan Montgomery complaining about free agency when he’s making $25 million (and will make an additional $22.5 million in 2025 once he opts out) and has a 6.25 ERA and negative 1.4 WAR is interesting,” said Jon Heyman of the New York Post. “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, it seems that when the (Boston Red Sox) suggested a willingness to sign a four-year deal, Montgomery never reached out to them…”

The “I’ve never had any contact with them” part could be the player’s fault, of course, but it’s Boras who’s written all over it. You know who else was open to a four-year deal? The Yankees.

“Montgomery also turned down a four-year, $72 million deferred offer from the Yankees, and the Arizona deal was probably better. But in hindsight, he most likely could have gotten more money in Boston,” the MLB insider wrote.

Boras has been criticized by many fans, pundits and even people in the baseball industry for the way he handled free agency with certain players, and Montgomery was one of them. Yes, he makes $25 million in 2024, but he could have signed a better and longer contract without his agent.