Red Sox

Montgomery said he would have considered playing in Boston if the Red Sox had made him an offer last winter.

Last winter was a long one for Jordan Montgomery. In an offseason full of rumors linking him to the Red Sox, the left-handed starting pitcher finally agreed to a contract with the Arizona Diamondbacks on March 26, two days before the start of the 2024 MLB regular season.

Montgomery accused his former agent Scott Boras on Friday of “messed up” the offseason and failing to close a deal with Boston in time.

“I had a Zoom call with (the Red Sox), that’s really all I know. It went well,” Montgomery told the Boston-Herald‘s Mac Cerullo ahead of the Red Sox’s series against the Diamondbacks this weekend at Fenway Park. “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 fired Boras on April 11 and hired Wasserman agents to represent him.

Boston was reportedly the favorite to sign the 31-year-old on March 4, just weeks before he landed with the Diamondbacks. The Red Sox and Montgomery were repeatedly linked throughout the offseason; the team desperately needed a starting pitcher and the pitcher was exactly what Boston needed.

Although one report claimed that Montgomery did not want to sign with the Red Sox after signing with Arizona, he told Cerullo he would have been interested in playing in Boston.

“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.”

He also said that, to his knowledge, the Red Sox never offered him a contract.

Entering last offseason, Montgomery was on the verge of breaking the bank as a free agent. He was fresh off the 2023 season in which he won the World Series with the Texas Rangers. Montgomery posted a 2.90 ERA in five starts over 31 innings in the playoffs, striking out 17 batters and allowing just five walks in those key appearances.

Montgomery signed a one-year, $25 million contract with the Diamondbacks, a deal that may be far from his expectations after helping lead the Rangers to their first World Series title.

But the starter has struggled this season in Arizona. Montgomery has a 6.44 ERA and a 1.67 WHIP in 19 starts over 95 innings. Batters are batting .315 against him and he is on pace to allow the most runs of his MLB career (he allowed 75 over 188 ⅔ innings last year and has already allowed 70 in 2024).

Montgomery’s struggles on the mound this season, coupled with a contract that is certainly far from what he wanted, rightly leave him with a bad taste in his mouth toward his ex-agent as he visits Fenway for the first time this season.