On paper, bringing Jordan Montgomery to the Red Sox made perfect sense. The left-hander had just won the World Series and seemed to be exactly the reinforcement the Red Sox needed. In the offseason, he even lived in Boston while his wife completed a residency in dermatology.
But as the weeks and months went by, no deal was reached and Montgomery signed with the Arizona Diamondbacks right at the start of the season.
Montgomery, who is returning to Boston for the first time this season, admitted that he would have liked to sign with the Red Sox, but expressed disappointment with the way his former agent, Scott Boras, handled his free agent.
“I had a Zoom call with (the Red Sox), that’s really all I know. It went well,” Montgomery said. “I don’t know, obviously Boras kind of messed it up, so I’m just trying to put the offseason behind me and forget about it.”
Montgomery was one of four Boras clients expected to land big free deals this past offseason. The others were left-hander Blake Snell, outfielder Cody Bellinger and third baseman Matt Chapman. None of them signed until well into the offseason, and all had to settle for short-term deals that fell far short of their expectations.
Montgomery was the last of the Boras Four to sign, signing a one-year, $25 million deal with the Diamondbacks that also included an option for 2025. Shortly thereafter, he released Boras and opted to complete his contract with rival agency Wasserman.
According to sources, LHP Jordan Montgomery has hired Joel Wolfe and Nick Chanock from Wasserman as his agents.
Montgomery was one of the Boras Four who did not sign a contract until shortly before the end of free agency.
I had predicted he would get 5 years and $106 million, and on March 26th he finally signed with Arizona for 1 year and $25 million.
— Kiley McDaniel (@kileymcd) 11 April 2024
The failure in free agency cost Montgomery tens of millions of dollars in the short term and could have a negative impact on his career in the long term.
Because Montgomery signed just before Opening Day, he didn’t get formal spring training and needed three weeks to get ready to play before making his debut on April 19. His performance has suffered accordingly, and in 19 starts, Montgomery has posted a 6.44 ERA in 95 innings. On Friday, the club announced he was being moved from the starting lineup to the bullpen.
Although he’s set to make $22.5 million next year anyway, according to contract details released by MLB.com’s Mark Feinsand, it’s unlikely Montgomery will ever be in as good a position to cash in as he would have been this winter as a soon-to-be 31-year-old after the best season of his career.
Would things have turned out differently if the Red Sox had pulled out their checkbooks last offseason? There’s no way to know, but although Montgomery said the club never put a formal offer on the table — “not that I know of,” he said — he would have considered it if they had.
“Yes, definitely. My wife and I have loved it here. She was at Beth Israel for a year, loves the area, loves the fans,” Montgomery said. “It would have been great if it had worked out that way, but it didn’t.”
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