In the world of Major League Baseball, free agency can be a fickle beast. One moment a player is fielding lucrative offers, and the next, their market inexplicably dries up. As the Jordan Montgomery free agency saga continues to unfold, the veteran pitcher remains unsigned. With Spring Training’s wind down, the Opening Day is just a few weeks away—a scenario that has piqued the interest of savvy baseball observers. Could the New York Yankees capitalize on the southpaw’s lingering free agency and potentially snag him on a bargain deal?

The Bombers are no strangers to Montgomery, having traded him to the St. Louis Cardinals in 22’s deadline deal. Now, with their ace Gerrit Cole sidelined by an elbow injury, a reunion in the Bronx suddenly seems like a plausible scenario.

The Boston Red Sox are reportedly the favorites to sign him, yet ownership’s concerns about a long-term contract have stalled negotiations. Jon Heyman of The New York Post suggested, “At one time the Red Sox may have responded by signing a big free agent. How about left-hander Jordan Montgomery…?” He added that the Red Sox seem reluctant to offer the seven-year deal Montgomery seeks.

The severity of Gerrit Cole’s elbow injury has cast a shadow over the Yankees’ starting rotation. Cole, a perennial Cy Young contender, is expected to miss at least the first month or two of the season. Signing Montgomery would trigger a 110% tax penalty for the Bombers, doubling his $30 million asking price and costing the team a whopping $63 million in gross payment.

This leaves the Yankees scrambling for pitching depth—a need Jordan Montgomery could potentially fill. While he’s not an exact replacement for Cole, his steady presence and postseason experience would be a valuable asset as the Yankees navigate the early part of the season. But would the Yankees, notoriously wary of hefty luxury tax penalties, be willing to open their wallets for their former pitcher?

Read More: What is Jordan Montgomery’s Net Worth?

Furthermore, Montgomery’s potential return could have a ripple effect on the Yankees’ pitching plans. Young arms vying for a rotation spot might suddenly find themselves with increased competition. And then there’s the lingering question of how Cole’s injury could impact the team’s overall strategy, perhaps putting a potential Montgomery reunion even higher on their priority list.

Competition and Jordan Montgomery’s Market

Montgomery is not without suitors, despite the slow pace of his free agency. The Boston Red Sox are reportedly the favorites to sign him, yet ownership’s concerns about a long-term contract have stalled negotiations. Jon Heyman of The New York Post suggests, “At one time the Red Sox may have responded by signing a big free agent. How about left-hander Jordan Montgomery…?” He adds that the Red Sox seem reluctant to offer the seven-year deal Montgomery seeks.

Meanwhile, the Texas Rangers, fresh off their World Series win, would like to bring their champion back to Arlington. However, several market reports state that owner Ray Davis is holding out on approving the deal, potentially for financial reasons. This hesitancy on both fronts presents the Yankees with a unique opening.

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Montgomery, for his part, is seeking a long-term deal, which could be a sticking point for any potential suitor. “I need Hal Steinbrenner to step up and say ‘This year is important to me, this is a 15-year drought, bring one of these guys in, I don’t care about the tax, it’s worth it,’” remarked American sports personality Keith McPherson. 

But could the Yankees, known for their occasional frugality (especially in recent years), be swayed by Montgomery’s price tag and demands? With Cole’s injury, a lack of clarity in Montgomery’s market, and the potential for a bargain, the Bronx Bombers could be tempted to make a play for their former southpaw. 

Whether they actually pounce on this opportunity remains to be seen. Montgomery’s future hangs in the balance. The Pinstripes face a pivotal choice: will they reunite with their former ace or let this opportunity slip away?

Read More: Limited Spring Training Could Stunt Blake Snell & Jordan Montgomery’s Synergy With New Teams