From the outside, for a period of months, free agent left-hander Jordan Montgomery has looked like a perfect fit for the pitching-needy Red Sox. The Red Sox, however, didn’t share that sentiment, and on Tuesday night, they watched him come off the board as the last big-name free agent of the offseason.
Two days before Opening Day, Montgomery agreed to sign with the Diamondbacks, as first reported by ESPN’s Jeff Passan. It’s a short-term deal, with Arizona guaranteeing one year at $25 million while adding a $25 million vesting option for 2025.
According to reports, Montgomery’s option vests for $20 million if he makes just 10 starts in 2024 (a very achievable number), with $2.5 million added to his 2025 salary at 18 starts and 23 starts. Montgomery can also opt out of the deal if he hits the 10-start mark this season.
Montgomery, who helped lead the Rangers to a World Series title over the Diamondbacks last fall, is the last top rotation domino to fall in a winter that has seen Yoshinobu Yamamoto (Dodgers), Blake Snell (Giants), Aaron Nola (Phillies), Eduardo Rodriguez (Diamondbacks), Sonny Gray (Cardinals), Shota Imanaga (Cubs), Marcus Stroman (Yankees) and others sign big free agent deals. Dylan Cease (Padres) and Tyler Glasnow (Dodgers) were traded.
The Red Sox entered the winter looking poised to make major upgrades to a rotation that struggled in 2023 but ended up simply swapping out Lucas Giolito (who will miss the season after undergoing elbow surgery months after signing a two-year, $38.5 million deal with Boston) for Chris Sale (who was traded to Atlanta for Vaughn Grissom).
The Red Sox will enter the 2024 season with five starters who were all on the team last year in Brayan Bello, Nick Pivetta, Kutter Crawford, Tanner Houck and Garrett Whitlock.
Outside of Yamamoto, who signed a $325 million deal with Los Angeles after a coast-to-coast bidding war broke out in December, Montgomery seemed like a logical fit to be Boston’s top target on the free agent pitching market. His profile as a durable veteran (Montgomery logged 188⅔ innings last year and has pitched at least 157 innings in each of the last three years) fit what the Red Sox appeared to need. Logistically, the Red Sox made sense for him as well; Montgomery’s wife is a dermatology resident at an area hospital and the pitcher spent much of the winter in Boston working out and throwing at Boston College.
Those logistics mattered little when compared to the financial aspects of any talks with the Red Sox. From early in the offseason, many in the industry expected the Red Sox to completely sit out of the high end of the free agent market in a stark departure from chairman Tom Werner’s promise that the team would go “full throttle” in its attempts to improve for 2024. At some point early in the winter, principal owner John Henry set a hard budget that largely eliminated the possibility of big-ticket additions, a notion all but confirmed by team president/CEO Sam Kennedy at the beginning of spring training when he acknowledged “set parameters” under which chief baseball officer Craig Breslow was working.
