Red Sox Predicted to Finally Upgrade Rotation With World Series Champ

jordan montgomery

Getty The Red Sox are in desperate need of making a big splash to help the roster. Landing hurler Jordan Montgomery is a good place to start.

As the MLB offseason got underway in November, Boston Red Sox fans had a reason to believe the winter would include some big acquisitions. That hasn’t happened yet, but it could change if they land free-agent starting pitcher Jordan Montgomery.

Bleacher Report’s Kerry Miller shared fresh predictions for the remaining unsigned players still on the open market as of February 18. When it came down to Montgomery, he predicted that Boston would finally make a headline-grabbing move and land the southpaw.

“The Boston Red Sox have an estimated $54 million to spend,” Miller said. “They desperately need another starting pitcher. Montgomery has had proven success in the AL East from his former time with the Yankees. And the real kicker is that his wife reportedly started her dermatology residency at a hospital in Boston, so he’s going to be spending a lot of time in Massachusetts anyway.”

MLB Trade Rumors predicted a six-year, $150 million deal for Montgomery on November 6. However, it’s also been reported that agent Scott Boras has been using Aaron Nola’s seven-year, $172 million deal with the Philadelphia Phillies as a benchmark in talks.

Rafael Devers Is Fed up With Boston’s Inaction

As Craig Breslow was getting settled into his new position as Boston’s head baseball chief, Red Sox chairman Tom Werner made a promise he’d probably like to take back. He told the media, including The Boston Globe’s Alex Speier, on November 2 that the club would go “full throttle” to improve the roster ahead of 2024.

But now that spring training is underway, Boston’s most significant move included signing starting pitcher Lucas Giolito to a two-year, $38.5 million deal. It’s been a frustrating offseason to sit through for Red Sox fans and players alike.

Third baseman Rafael Devers spoke to the media on February 20. He put the front office on notice with his comments regarding the club’s lack of action.’s Ian Browne shared what the left-handed slugger said through an interpreter.

“They need to make an adjustment to help us players to be in a better position to win,” Devers said. “Everybody in this organization wants to win, and we as players want to win, and I think they need to make an adjustment to help us win.

“Everybody knows what we need. You know what we need, and they know what we need. … Everybody who knows the organization or knows the game knows what we need.”

Would Montgomery Even Sign With Boston?

No MLB team has won more World Series titles than the Red Sox this century. They’ve climbed to the top of the baseball world four times, with 2018 being the most recent occurrence. Times have been tough for the organization lately, though.

Boston reached the American League Championship Series in 2021, eventually losing to the Houston Astros. Outside of that, they’ve finished in last place in the AL East three times since 2020. That includes each of the past two seasons. Baseball Prospectus’ PECOTA projections are expecting more of the same from manager Alex Cora’s club in 2024 with another last-place finish.

Adding Montgomery would bring a productive and dependable starter to pair with Giolito. Would he even be interested in playing for the Red Sox, though?

“The Red Sox, according to sources, have kept tabs on Montgomery’s market,” Speier reported on February 13. “But if it does collapse in a way that makes him available on a shorter-term deal, there’s an industry belief that he’d be more likely to head to a team with a better chance to win in 2024 than the Red Sox. So, not impossible, but highly unlikely.”

If the Red Sox sincerely do want to sign Montgomery, it seems like they have their work cut out for them.

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