“Jordan Montgomery’s Rough Season and the Agent Misstep That Cost Him a Red Sox Deal”
Last winter was a tough one for Jordan Montgomery. Despite numerous offseason rumors connecting him to the Red Sox, the left-handed pitcher ultimately signed with the Arizona Diamondbacks on March 26, just two days before the start of the 2024 MLB season.
On Friday, Montgomery criticized his former agent, Scott Boras, for mishandling the offseason negotiations and failing to secure a timely deal with Boston.
“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 before the Red Sox’ series against the Diamondbacks at Fenway Park this weekend. “Obviously, Boras kind of messed it up, so I’m just trying to move on and forget about the offseason.”
Montgomery parted ways with Boras on April 11 and hired new representation from Wasserman.
On March 4, Boston was reportedly the front-runner to sign the 31-year-old, just weeks before he ended up with Arizona. The Red Sox were consistently linked to Montgomery throughout the offseason, as the team was in desperate need of starting pitching, and Montgomery was seen as a perfect fit.
Despite a report suggesting that Montgomery wasn’t interested in signing with the Red Sox after his deal with Arizona, he told Cerullo he would have been open to playing in Boston.
“Yeah, definitely. My wife and I loved it here. She spent a year at Beth Israel, we love the area and the fans,” Montgomery said. “It would have been great if it worked out that way, but it didn’t.”
He also mentioned that, to his knowledge, the Red Sox never formally offered him a contract.
Heading into the offseason, Montgomery was expected to land a lucrative deal after helping the Texas Rangers win the 2023 World Series. In the playoffs, he posted a 2.90 ERA in five starts over 31 innings, striking out 17 and walking just five in high-pressure situations.
Montgomery eventually signed a one-year, $25 million contract with the Diamondbacks, which likely fell short of his expectations after his World Series success.
This season, Montgomery has struggled with Arizona, posting a 6.44 ERA and 1.67 WHIP in 19 starts over 95 innings. Opposing hitters are batting .315 against him, and he’s on pace to allow the most runs of his career (he allowed 75 last year over 188 2/3 innings and has already given up 70 in 2024).
Diamondbacks manager Torey Lovullo announced on Friday that Montgomery will be moved to the bullpen due to his struggles.
Montgomery’s disappointing performance this season, combined with a contract that likely fell short of his expectations, has left him understandably frustrated with his former agent as he returns to Fenway for the first time this season.