Will the Boston Red Sox sign Jordan Montgomery in MLB free agency? Rumors swirled throughout the offseason about Boston's Montgomery pursuit, yet nothing has come to fruition and spring training has already begun. MLB insider Peter Gammons provided an intriguing update on Boston's Montgomery pursuit Monday.

“One NL executive yesterday said ‘we hear the Red Sox and Scott Boras had a good meeting recently and may get some deal eventually done on Jordan Montgomery,'” Gammons wrote on X (formerly Twitter).

Adding pitching is of the utmost importance for Boston. It is an area where they have struggled in previous seasons. The Sox signed former All-Star Lucas Giolito this past offseason, but adding Montgomery still makes a lot of sense.

Red Sox general manager Craig Breslow is rumored to be prioritizing pitching additions via other strategies as well.

“Another said ‘we've seen Craig Breslow really working hard to acquire young power arms to build pitching. You can bet their first four picks in the draft with be pitchers,'” Gammons reported.

Still, it would feel like a letdown for Red Sox fans if Boston fails to sign Montgomery in MLB free agency. MLB insider Buster Olney of ESPN thinks Boston can certainly make a deal come to fruition.

“The Red Sox had a zoom meeting with Jordan Montgomery recently. He’d represent an upgrade for their ‘24 rotation, and if signed to a long-term deal, could be part of the staff rotation. They certainly have the payroll flexibility to make it happen,” Olney wrote on X.

The fit unquestionably works for both Montgomery and the Red Sox. Boston has displayed hesitancy in signing free agents over the past few years, however. Montgomery is a reliable starter with ace potential, and signing him would give the Sox much better odds of contending in 2024.