Red Sox Could Land Free Agent Pitcher Thanks to Family Connection: Insider

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Starting pitcher Jordan Montgomery hoists the World Series trophy for the Texas Rangers in 2023

MLB insider Jon Heyman reported on January 24 that the Boston Red Sox have a “good possibility” of landing top free agent pitcher Jordan Montgomery if he doesn’t return to the Texas Rangers because of his wife’s connection to the city.

“The other team that I think is a good possibility for Montgomery if it doesn’t work out in Texas would be Boston,” Heyman said in a video posted on X. “His wife is, I believe, (in) medical school or in residency I think connected to Harvard… and I hear that the Red Sox certainly do like Montgomery very much.” 

Montgomery’s wife, McKenzie Dirr, earned a degree from the University of South Carolina School of Medicine and studied at Harvard’s department of dermatology before beginning residency at a hospital in Boston. The couple recently moved there and Montgomery has been working out at Boston College this offseason.

Now that connection might give the Red Sox an inside edge on adding Montgomery, one of the most coveted pitchers left on the market.

“He’s gonna be in very good shape, people like him, he’s trending up, very durable, very clutch,” Heyman said.

Jordan Montgomery’s Ace Status for the Boston Red Sox

After a stellar season in 2023 that saw Montgomery pitch for a 3.20 ERA, 166 strikeouts and 10 wins in 188.2 innings for both the St. Louis Cardinals and Rangers and ended with a World Series trophy, he is one of the most enticing pitchers left on the free agent market.

Montgomery would instantly jump to the top of a rotation in Boston that currently includes Lucas Giolito, Nick Pivetta, Brayan Bello, Kutter Crawford and Tanner Houck. He would add some much-needed strikeout potential to back up an offense that performed better than the team’s 78-84 record for 2023 suggests.

Other Likely Moves for the Boston Red Sox This Offseason

The Red Sox have been connected to a broad range of free agents, but haven’t made any splashy moves this offseason. The team has indicated that they are unlikely to spend much more money than they did last season, despite their poor record.

“Speaking prior to Red Sox Winter Weekend, the CEO (Sam Kennedy) told the media the team’s payroll for this season will ‘probably be lower’ than it was in 2023,” Boston.com reported. “The payroll last year was $225 million.”

While the Sox have an inside chance to add Montgomery, they might opt to add a cheaper option instead.

“The club has been connected to some big name free agents that are still available, such as Blake Snell and Jordan Montgomery, but perhaps they need to free up a bit of cash before they can earnestly pursue any of those,” MLB Trade Rumors reported. “More affordable options would include Mike Clevinger, Michael Lorenzen, Hyun Jin Ryu and others.”

The Red Sox are also rumored to want a reunion with free agent slugger Adam Duvall. Duvall could give them some lineup power in the absence of any larger acquisitions and could play a role in mentoring a young core of prospects that might make strides toward the big league if Boston chooses a frugal route for 2024.