Just-in: Jordan Montgomery finally off board as quiet Red Sox winter officially ends
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, watched him come off the board as the last big-name free agent of an endless offseason.
Just 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, 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), Shōta Imanaga (Cubs), Marcus Stroman (Yankees) and others sign big free agent deals while 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 188 ⅔ innings last year and has pitched at least 157 frames 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; as MassLive reported in late November, 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.
Once the Red Sox signaled that their focus, while trying to stay nominally competitive in 2024, was on the future, it became clear that they would not be seriously involved in the markets for late signees like Montgomery or Snell if those pitchers would up taking short-term deals. Considering that long-term view, a pact similar to the one Montgomery signed with the Diamondbacks (the reigning National League Champions) would not have fit within the down-the-road contention window the Red Sox believe they have.
The Red Sox did stay in touch with Montgomery and his representatives at Boras Corporation throughout the winter and had at least one Zoom meeting with him in early February. Those around the game never viewed the club to be seriously involved in the bidding despite the logical fit on paper.
