Yankees Predicted for Reunion With Free Agent Pitcher Seeking $172 Million Deal

Jordan Montgomery

Getty Free agent pitcher Jordan Montgomery was traded away by the New York Yankees but the two might be poised for a reunion in 2024.

The New York Yankees had questions about their rotation depth even before franchise ace Gerrit Cole was hit with a surprise elbow injury that projects to keep him off the mound for at least the first few weeks of the season.

After missing out on adding reigning Cy Young winner Blake Snell, who joined the San Francisco Giants, the Yankees have now been predicted to answer those questions by signing the best remaining pitcher on the market, Jordan Montgomery. 

“I think Montgomery will ultimately end up in New York where it all began for him,” Ben Verlander projected for Fox Sports. “With the news of Gerrit Cole out for maybe three months, the Yankees need someone to fill the void in that rotation and Montgomery is a great fit.”


The New York Yankees and Jordan Montgomery Have a History

Montgomery launched his big-league career in the Bronx, pitching five full seasons with the Yankees before being traded to the St. Louis Cardinals in 2022. While he was serviceable in New York, his career has surged since leaving, marked by a World Series championship last season with the Texas Rangers. In 2023, Montgomery pitched for a career-best 3.20 ERA and 166 strikeouts in 32 starts.

While a reunion could make sense on paper, with Montgomery possessing the best available arm and the Yankees having perhaps the greatest need to add one, the cost of the reunion could be a sticking point.


New York Yankees’ Pitching Target Jordan Montgomery Is Seeking a Contract in the Range of $172 Million

“Montgomery’s camp compares him to Aaron Nola, who got $172 million over seven years,” Jon Heyman of the New York Post reported, adding that “sources say they are back in contact” though there is a “gap” in negotiations.

While that’s a high cost for a Yankees team that is already facing a significant luxury tax hit, the team likely wants to avoid new deals with high annual average values (AAVs) rather than smaller salaries over the long term. 

The Yankees offered Snell a six-year, $150 million deal before he went with a high-AAV deal with an opt out in San Francisco, according to USA Today’s Bob Nightengale. They might now be willing to extend a similar offer to Montgomery.

Then there is the question of whether or not Montgomery would be open to returning to the team that traded him away for little in return. Montgomery might hold some bitter feelings about that, but the Yankees found a way to add veteran pitcher Marcus Stroman this offseason despite their own public issues.

“There’s a clear on-paper fit for a return to the Bronx,” Anthony Franco wrote for MLB Trade Rumors. “While Montgomery had some parting shots for the front office after being traded to St. Louis at the ’22 deadline, Stroman had also publicly criticized the Yankees before signing his deal.”

If the Yankees do reach a deal with Montgomery, he would likely become the team’s rotation leader until Cole returns. With Opening Day looming, he almost certainly wouldn’t be ready at the start of the season either, but there’s little question that he can eat a lot of innings for whatever team he joins next.

“Montgomery probably wouldn’t step into the Opening Day rotation given his lack of competitive Spring Training work, but he has been incredibly durable since undergoing Tommy John surgery in 2018,” per Franco.

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