Red Sox waiting game in free agency could ruin their Jordan Montgomery chase

The free agent and recent World Series champion is a high-profile target for many teams this offseason.

Oct 28, 2023; Arlington, TX, USA; Texas Rangers starting pitcher Jordan Montgomery (52) warms up
Oct 28, 2023; Arlington, TX, USA; Texas Rangers starting pitcher Jordan Montgomery (52) warms up / Kevin Jairaj-USA TODAY Sports
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Jordan Montgomery helped the Texas Rangers to their first World Series title in franchise history this past season. He made six appearances, five of them starts, during their playoff run, and registered a 2.90 ERA after performing admirably down the stretch after being acquired at the trade deadline.

Montgomery is now a free agent spending his offseason living in Boston with his wife who is serving a dermatology residency. And the local team, the Boston Red Sox, would certainly improve their rotation by signing him.

The Sox have been connected to Montgomery throughout the offseason, but other teams need starting pitching help, and it doesn't help Boston's front office is hamstrung by having to get money off the payroll.

It also doesn't help Jon Heyman of the New York Post believes the Rangers are the most likely to sign Montgomery. And his reasons make sense. On a live stream for Bleacher Report on Jan. 3, Heyman stated that Montgomery's playoff showing for Texas is a huge factor in the potential reunion, and that the local TV deal is moving along which could help the financing.

According to Heyman, Texas' broadcast woes may be approaching resolution, which means they could soon shift their focus to more important things: free agency.

Could the Rangers steal Jordan Montgomery from the Red Sox?

It's clear why Texas would want Montgomery back after his World Series run — his numbers were high quality and the Rangers were finally able to compete with and defeat baseball's villain in the Houston Astros.

The left-hander remains in high demand across the league. On the Dec. 29 episode of MLB Network's High Heat, Heyman said the Red Sox are "in play" for Montgomery, along with the Mets, Yankees and others. But if Boston wanted a chance, they probably would've had to strike earlier rather than letting all the other contenders hang around as they lost out on other assets.

There are only two remaining free-agent starters that could adequately fill the holes in the Sox's rotation: Montgomery and 2023 National League Cy Young Award winner Blake Snell. SNY's Andy Martino recently shared that Snell has expressed interest in playing for the Yankees, and Snell would likely expect a paycheck that Boston's front office would be unwilling to cash.

If Boston is serious about signing another starter to bolster its rotation this season, it needs to take its pursuit of Montgomery more seriously. The Sox would need to free up a spot on the 40-man roster and trade someone like reliever Kenley Jansen, who is owed $16 million next season. Some would argue Montgomery is the better long-term fit and investment than Snell,

Now that the Rangers are nearly ready to focus back in on baseball instead of broadcasting rights, the Red Sox don't have any more time to waste. Same goes for the Yankees now that they're no longer distracted by Yoshinobu Yamamoto. Craig Breslow and Co. need to act fast and figure out a way to clear payroll later down the road because the longer they wait, the less likely they'll end up with what they want.

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