Details from Jordan Montgomery’s free agency decision should motivate Red Sox

After the fateful Zoom call between the Boston Red Sox and Jordan Montgomery's team in mid-February, many Red Sox fans believed the pitcher was destined for Beantown.

But after months of rumors and waiting, the lefty signed elsewhere, and his decision broke some Bostonian hearts.

Montgomery spent all offseason asking for quite a deal — somewhere in the seven-year range. There weren't many clubs chomping at the bit to sign a 31-year-old pitcher for such a stretch, so the veteran lessened his range. But that choice officially knocked the Red Sox out of the running for his signature.

A recent piece by MLB insider Jon Heyman revealed that Montgomery wasn't interested in playing for the Red Sox because he wants to win games if he was going to sign a short-term deal. Players and management staff skipping out on the Red Sox because of their recent poor run of form, and it reveals another flaw in John Henry's small-market spending plan — you know, besides the three last-place finishes in four years thing.

Jordan Montgomery didn't want to play for the Red Sox because he wished to pitch for playoff contenders

If Montgomery was going to be forced to sign a short-term contract, he wanted it to be with a postseason contender — the pitcher needs to continue pitching in big moments to hopefully secure the big-ticket deal he wants next offseason. Boston hasn't been in the playoff conversation in recent years, as Sox fans know all too well.

Boston's front office believes it competed for the services of Shohei Ohtani and Yoshinobu Yamamoto, among other free agents this winter. But the players it targeted were attracted to teams with star power, and the Red Sox don't have much to show for in that category. Rafael Devers alone is not going to draw other talented players to Boston.

Surely Henry knows this because it seemed like he and Fenway Sports Group had no plans to spend on top-tier outside help in the first place. But the Red Sox showed in spring training and on Opening Day that all they would need to contend for a playoff spot is quality starting pitching like they were promised this winter. Montgomery and another competent third or fourth starter would bring Boston into the playoff conversation.

But, if the Red Sox can carry their hot streak into the season and secure a playoff spot, Montgomery may give Boston a second thought next year. For now, though, the team should be motivated by Monty's decision, knowing if they play hard this year, their free agency fortunes could change by November.

More Red Sox reads: