The New York Yankees made significant improvements to their roster after a disappointing 82-80 performance in 2023. Expectations are high for 2024 as Opening Day draws closer. Could another acquisition for the rotation happen by way of a reunion with southpaw Jordan Montgomery?

Most of the rumors surrounding the Yankees possibly making another free-agent move have centered on two-time Cy Young winner Blake Snell. However, his openness to a short-term deal with opt-outs has made an agreement with the Bombers unlikely. Montgomery isn’t ready for that type of contract yet, though.

According to a March 7 report from Jon Heyman of the New York Post, the 2023 World Series champion is still searching for a long-term contract. FanSided’s Josh Wilson notes that Monty’s contract preference “might work out nicely for New York.” If the southpaw signs a longer-term deal in the Bronx, it’d allow general manager Brian Cashman to minimize the potential luxury tax hit.

Spotrac is projecting a six-year, $110 million deal for Montgomery. Even if a deal landed closer to Aaron Nola’s seven-year, $172 million pact with the Philadelphia Phillies, that’d be a more palatable yearly expense. Plus, New York wouldn’t have to surrender any 2024 MLB Draft picks or international bonus pool money because Montgomery didn’t receive a qualifying offer.

Montgomery Would Help the Yankees’ Rotation Depth

The Yankees’ projected Opening Day rotation includes Gerrit Cole, Carlos Rodón, Marcus Stroman, Nestor Cortes and Clarke Schmidt, per FanGraphs’ Roster Resource. If all goes right, this could be a good unit. However, Cashman knows depending on the best-case scenario could be a mistake.

SNY’s Andy Martino reported on February 5 that New York wasn’t totally satisfied with its pitching upgrades. He also speculated that another move before Opening Day isn’t out of the question. Rodón’s shaky spring as he hopes to bounce back following a horrific 2023 may force the club’s hand. Through 5.2 innings, he’s allowed four runs on six hits (three home runs), three walks and six strikeouts.

Montgomery would bring a sense of certainty to the Yankees’ rotation. He’s made 30-plus starts in each season since 2021. Across the southpaw’s most recent 524.1 innings, Monty has twirled a 3.48 ERA and 1.18 WHIP with 486 strikeouts. The lefty also knows what it’s like to pitch in New York. He was drafted by the Yankees in 2014 and spent parts of six seasons with the Bombers.

Red Sox Might Opt for Other Rotation Options

For a while, the Boston Red Sox seemed to be a likely landing spot for Montgomery, but Lucas Giolito could be sidelined for all of 2024. So, the squad might now be looking elsewhere for rotation upgrades. Another report from Heyman suggests Boston could instead be eyeing a “solid innings eater” like Michael Lorenzen or Mike Clevinger.

It was already debatable as to whether Montgomery would even seriously consider signing with the Red Sox. They’ve finished in last place three times since 2020, including each of the last two seasons.

“The Red Sox, according to sources, have kept tabs on Montgomery’s market,” Alex Speier of the Boston Globe reported on February 13. “But if it does collapse in a way that makes him available on a shorter-term deal, there’s an industry belief that he’d be more likely to head to a team with a better chance to win in 2024 than the Red Sox. So, not impossible, but highly unlikely.”

Can the Yankees swoop in and reunite with their former homegrown hurler? If they do, it’d be a boon to New York’s rotation while also sticking it to the Red Sox.