Jordan Montgomery To Red Sox? Making Case For Late-Offseason Splash

The Boston Red Sox entered the offseason in desperate need of frontline starting pitching to upgrade the rotation.

Boston did make a solid signing, bringing in former All-Star Lucas Giolito to pair with Brayan Bello. In reality, the Red Sox needed to add two pitchers, finding themselves right back in that position after trading Chris Sale to the Atlanta Braves, though that move did fill a hole at second base with youth in Vaughn Grissom.

Arms such as Bello, Giolito, Nick Pivetta and Kutter Crawford appear to be locks for the Red Sox rotation, all proving their worth as starters in previous seasons. The current roster construction would create a competition among Garrett Whitlock, Tanner Houck and Josh Winckowski, who shined as a reliever in 2023, for the final rotation spot.

All three of those pitchers have enjoyed plenty of success as exceptional arms in the bullpen. The Red Sox could get the most out of the trio if the organization makes a final offseason move. Luckily, a legitimate starter remains on the market.

Jordan Montgomery went to free agency with as much momentum as a pitcher could ask for after pushing the Texas Rangers to a World Series championship. During his postseason run, the lefty went 3-1 with a 2.90 ERA as an anchor of the Texas rotation.

Throughout his career, Montgomery has excelled in the middle of the rotation, not normally emerging as a frontline starter until this past postseason. His playoff performance may earn him an ace-level paycheck, but that often hasn’t been his role, though that could change with the Red Sox.

Given the Red Sox rotation at the moment, however, Montgomery can elevate as a 1-2 punch at the top with Giolito. The 31-year-old consistently takes the ball and gives his team a chance to win. Over his last three seasons, Montgomery has made at least 30 starts with a sub-4.00 ERA in each of those years.

That production gives Boston exactly what the team missed in 2023 with a staff that tallied the fourth-fewest innings in the majors. Not only does Montgomery post when it’s his turn to take the ball, but he’ll keep the Red Sox in games, giving a young lineup the chance to make noise.

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Signing Montgomery adds some hope for the Red Sox in 2024, giving Boston a full rotation of capable starters and taking pressure off of several other arms.

The season is approaching quickly as pitchers and catchers report to spring training next week. That should not prohibit the Red Sox from making an impact signing to start camp. The chance to add Montgomery is right in front of them, especially given Montgomery’s current living situation in Boston with his wife working a residency at a city hospital.

A deal between Montgomery and the Red Sox is a win-win for both sides. In the coming days, Boston has a favorable opportunity to add a legitimate starter should the front office be ready to make the deal.