It’s a baseball love triangle with a twist. Jordan Montgomery, the reliable lefty pitcher, is a hot free-agent commodity. The Boston Red Sox desperately need starting pitchers. And Montgomery’s wife is studying in the same city. On the surface, it all seems like the planets are aligning. But with Boston’s front office known for calculated maneuvers, will their notorious patience backfire in this case?

The Red Sox have a history of playing a slow and steady game, but that approach can cut both ways. Sometimes, it pays off. But other times, they might end up watching a coveted player slip through their fingers while they wait for the right moment. Will Gumby be the one who gets away?

Jordan Montgomery: The Ideal Red Sox Fit?

The Boston Red Sox are reportedly keen on acquiring Montgomery, as noted by both Rod Bradford of WEEI and Sean McAdam of MassLive, per market reports. The team sees the pitcher as a superior option to the remaining free agents, but they’re playing a waiting game, hoping the asking price will drop.

Jordan Montgomery’s connection to Boston goes beyond convenience; his wife, Dr. McKenzie Dirr-Montgomery, is conveniently pursuing a residency at a Boston hospital, which solidifies the appeal of playing in this city. But that is not all.

Read More: As Blake Snell’s Sweepstakes Stall, Could the Boston Red Sox Swoop in With a Crucial Offer?

Boston’s rotation stands in a state of flux. While they acquired Lucas Giolito, the Chris Sale trade left a significant hole. Replacing Sale isn’t about a one-for-one trade; it’s about bolstering the overall starting pitching depth. Will Montgomery help do just that?

A Matter of Patience, Price, and Competition

The Red Sox are characteristically patient and dealing with the pitcher’s agent, Scott Boras, on the down low, but according to McAdam, Jordan Montgomery’s asking price remains stubbornly high. That creates a dangerous waiting game.

Boston’s budget flexibility, with a competitive balance tax figure of $202 million, according to Roster Resource, gives ample room for a significant acquisition. But the moment that price drops, other teams will pounce. The Red Sox could easily lose the pitcher to a team willing to act more quickly.

Read More: Mets in Pitcher Hunt? Kodai Senga Injury Scare Signals Montgomery, Snell Pursuit

The Boston Red Sox and Jordan Montgomery appear tailor-made for each other. But with patience as a core tenet of Boston’s front office strategy, a sense of urgency may be the missing factor. Will their calculated approach yield the perfect pitcher, or will they watch him walk away to another team willing to be slightly less patient? Only time will tell.