Jordan Montgomery’s reason for not signing with Red Sox is depressing but valid

Jordan Montgomery agreed to terms for a contract with the Arizona Diamondbacks. The one-year deal is worth $25 million and includes a vesting player option for 2025. Montgomery, who helped the Texas Rangers win their first World Series in franchise history, was the last remaining free agent of the "Boras Four."

Boston Red Sox fans, among others, weren't too pleased with the news. The Red Sox didn't seem too interested in acquiring the left-handed ace this winter, but it wouldn't have mattered anyway. Montgomery preferred not to sign with the Red Sox because he wants to win, according to Jon Heyman of the New York Post.

Jordan Montgomery wasn't interested in Red Sox, wanted to win

It's understandable that Montgomery wouldn't want to sign with Boston given their recent history. The Red Sox have finished last in the American League East for the past two seasons and they haven't done much to inspire confidence during their dormant winter. Boston signed just two major league free agents before spring training began.

After finishing the 2023 campaign with 78 wins, the Red Sox traded outfielder Alex Verdugo and left-hander Chris Sale. Boston will start Triston Casas and Vaughn Grissom in their place. They also extended 24-year-old pitcher Brayan Bello before his first Opening Day start.

The Red Sox were seen as a potential landing spot for the southpaw after it was reported that he was living in Boston and working out at Boston College. Montgomery's wife, McKenzie, started a dermatology residency at Beth Israel, a local hospital in affiliation with Harvard University. His wife is now transferring to Vanderbilt University in Nashville, Heyman reported.

Red Sox manager Alex Cora acknowledged that the club held a Zoom call with Montgomery at the start of spring training, as ESPN's Buster Olney reported. Discussions stalled after the call, and Montgomery turned his focus to other interested teams. Maybe their Zoom call disconnected after the 40-minute time restriction for free users. After all, would it be surprising if the Red Sox didn't pay for a license?

Montgomery played for both the St. Louis Cardinals and the Rangers last season, and he posted a 3.20 ERA in 188.2 innings. In six postseason games, Montgomery had a 3-1 record with a 2.90 ERA and 17 strikeouts. He helped shut down the Houston Astros in Game 1 of the ALCS.