After helping lead the Texas Rangers to their first World Series in franchise history, Jordan Montgomery had hefty expectations heading into the offseason, only to fail to sign with a team until after spring training and have one of, if not the worst, years of his career.

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Montgomery ultimately settled for a one-year, $25 million deal with the Arizona Diamondbacks—far from the long-term contract he initially sought. He has since been outspoken about how poorly his agent, Scott Boras, handled the negotiations, stating that Boras “butchered” the process. Despite this, recent reports suggest Montgomery had more options than just Arizona.

According to Jon Heyman of the New York Post, the New York Yankees extended a four-year offer worth around $72 million to Montgomery. Heyman remarked, “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.”

While it’s impossible to know how this season would have played out had Montgomery signed with the Yankees or Red Sox instead of the Diamondbacks, one could assume a change in scenery might have made a difference for the veteran left-hander.

Montgomery had experienced success with the Yankees earlier in his career, spending his first four seasons in New York. In 2021, he posted a solid 3.83 ERA across 30 starts

Heyman also noted that Montgomery was hesitant to sign with the Red Sox due to the length of their offer. With a four-year contract on the table, Montgomery reportedly didn’t like the Red Sox’s postseason outlook and was wary of being tied to a potentially non-competitive team.