Jordan Montgomery says 'Boras kind of butchered' his free agency

BOSTON — On paper, Jordan Montgomery to the Red Sox made perfect sense. The left-hander was coming off a World Series championship and seemed like the kind of front-of-the-rotation upgrade the Red Sox needed. He even lived in Boston over the offseason while his wife did a dermatology residency in the area.

But as the weeks and months went on no deal materialized, and Montgomery wound up signing with the Arizona Diamondbacks right as the season began.

Now back in Boston for the first time this season, Montgomery acknowledged he would have been interested in signing with the Red Sox while expressing disappointment with the way his free agency was handled by his former agent, Scott Boras.

“I had a Zoom call with (the Red Sox), that’s really all I know. It went good,” Montgomery said. “I don’t know, obviously Boras kind of butchered it, so I’m just trying to move on from the offseason and try to forget it.”

Montgomery was one of four Boras clients who were expected to land big deals in free agency this past offseason, with the others being fellow left-hander Blake Snell, outfielder Cody Bellinger and third baseman Matt Chapman. All remained unsigned until deep into the offseason, and all wound up settling for short-term deals that fell far short of their projections.

Montgomery was the last of the Boras Four to sign, inking a one-year, $25 million deal with the Diamondbacks that also included a vesting option for 2025. He fired Boras shortly afterwards, opting to switch representation to Wasserman, a rival agency.

The free-agency misfire cost Montgomery tens of millions of dollars in the short term, and it could wind up having a negative impact on his career over the long term as well.

Because Montgomery signed right around opening day, he didn’t get any kind of formal spring training and wound up needing three weeks to ramp up before debuting 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 rotation to the bullpen.

Though he’s in line to make $22.5 million next year regardless, according to contract details reported by MLB.com’s Mark Feinsand, it’s unlikely Montgomery will ever be in as good position to cash in as he would have been this winter as a soon-to-be 31-year-old coming off the best season of his career.

Would things have turned out differently if the Red Sox had opened their checkbooks this past offseason? There’s no way to know, but while 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.

“Yeah, for sure. Me and my wife loved it here. She was at Beth Israel for a year, love the area, love the fans,” Montgomery said. “It would have been awesome if it had worked out that way, but it didn’t.”