Top 5 Free Agents the Red Sox Must Target After Missing Out on Yoshinobu Yamamoto

Oct 28, 2023; Arlington, TX, USA; Texas Rangers starting pitcher Jordan Montgomery (52) throws a
Oct 28, 2023; Arlington, TX, USA; Texas Rangers starting pitcher Jordan Montgomery (52) throws a / Kevin Jairaj-USA TODAY Sports
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2. Jordan Montgomery

At least for oddsmakers, southpaw Jordan Montgomery and the Boston Red Sox are the most likely match — with the Red Sox sittings as the favorites on some sportsbooks.

Montgomery used a strong 2023 campaign to hike up his free-agent value. Between the St. Louis Cardinals and Texas Rangers, he compiled a career-best ERA, including a 2.79 ERA in 11 starts once arriving in Texas. Montgomery was an integral part of the Rangers' ALCS win over in-state rival Houston, as he started three games and went 2-0 with a 1.79 ERA, also picking up the win in Game 7.

Montgomery is currently living in Boston while his wife completes her dermatology residence at an area hospital. This information only further fueled speculation of a free agency marriage between him and the Red Sox.

The left-hander is reportedly using Carlos Rodon's contract with the New York Yankees last season as his comp in free agency. Brian Cashman signed Rodon to a six-year, $162 deal last season.

This seems like a steep price for Montgomery. When Rodon agreed to the deal, he was coming off two sub-three ERA seasons in which he received All-Star selections in both, as well as fifth and sixth-place Cy Young finishes. Montgomery's lowest season ERA is 3.20, and he has never earned an All-Star appearance or Cy Young votes. The only similarities between the two seems to be their age and which hand they throw the ball with.

Unfortunately for the Red Sox, they don't have a lot of wiggle room or leverage. Between their indisputable need to upgrade their rotation and their rock-bottom goodwill with the fanbase, they very much might have to overspend for Montgomery. The fanbase will continue to get impatient if the team comes out of this offseason with crumbs, and Boston doesn't have the talent in their rotation to strike a hard line in contract negotiations.

He's already living here, make it permanent Craig.