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ARLINGTON, TEXAS - OCTOBER 28: Jordan Montgomery #52 of the Texas Rangers pitches in the third inning against the Arizona Diamondbacks during Game Two of the World Series at Globe Life Field on October 28, 2023 in Arlington, Texas. (Photo by Sam Hodde/Getty Images)
ARLINGTON, TEXAS - OCTOBER 28: Jordan Montgomery #52 of the Texas Rangers pitches in the third inning against the Arizona Diamondbacks during Game Two of the World Series at Globe Life Field on October 28, 2023 in Arlington, Texas. (Photo by Sam Hodde/Getty Images)Sam Hodde/Getty Images

Yankees Must Pursue Jordan Montgomery Contract in Free Agency Amid Latest MLB Rumors

Zach BuckleyMar 22, 2024

After snapping a six-year playoff streak last season, the New York Yankees made a bold trade for slugger Juan Soto this offseason.

But the momentum created by that deal all but evaporated once ace pitcher Gerrit Cole, the reigning AL Cy Young winner, was lost to a worrisome arm injury since identified as nerve inflammation and edema. The Yankees, who sacrificed plenty of pitching depth in the Soto deal, aren't built to withstand the loss of Cole.

Few (if any) teams are.

Yet, the Yankees aren't hopeless. They just find themselves in significant need of a significant upgrade, and it just so happens that the free agent market still has one available. Jordan Montgomery, who opened his MLB career in pinstripes, remains unsigned after pitching to a 3.20 ERA last season and getting even stingier (2.90 ERA across 31 innings) come playoff time while helping steer the Texas Rangers to their first World Series title.

Montgomery's camp had spoken with New York earlier in the offseason, and Jon Heyman of the New York Post reported "they are back in contact."

It's time to get a deal done. The Yankees' hopes for this season could easily depend on it.

New York's Rotation Needs a Jolt

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TAMPA, FL - FEBRUARY 21: Gerrit Cole #45 of the New York Yankees during spring training at George M. Steinbrenner Field on February 21, 2024 in Tampa, Florida. (Photo by New York Yankees/Getty Images)
TAMPA, FL - FEBRUARY 21: Gerrit Cole #45 of the New York Yankees during spring training at George M. Steinbrenner Field on February 21, 2024 in Tampa, Florida. (Photo by New York Yankees/Getty Images)

MLB.com's Anthony Castrovince recently ranked the league's top 10 rotations. Actually, the scribe went even a little further than that, since his 10th spot featured a three-way tie between the Baltimore Orioles, Houston Astros and Miami Marlins.

The Yankees, as you may have surmised already, were excluded from that list.

And while they at least cracked the honorable mention section, their inclusion came with several caveats: "If and only if Gerrit Cole comes back quickly and Nestor Cortes and Carlos Rodón both bounce back, the Yankees belong."

That's hardly a ringing endorsement of this rotation, and who knows how many (if any) of those caveats will even come true. Yet, that's the state of this pitching staff, which will feature Cortes, who posted a 4.97 ERA across 63.1 innings last season, on the bump for Opening Day.

An Investment in Montgomery Feels Safe

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ARLINGTON, TX - OCTOBER 28:   Jordan Montgomery #52 of the Texas Rangers pitches during Game 2 of the 2023 World Series between the Arizona Diamondbacks and the Texas Rangers at Globe Life Field on Saturday, October 28, 2023 in Arlington, Texas. (Photo by Daniel Shirey/MLB Photos via Getty Images)
ARLINGTON, TX - OCTOBER 28: Jordan Montgomery #52 of the Texas Rangers pitches during Game 2 of the 2023 World Series between the Arizona Diamondbacks and the Texas Rangers at Globe Life Field on Saturday, October 28, 2023 in Arlington, Texas. (Photo by Daniel Shirey/MLB Photos via Getty Images)

Safety is, of course, a relative term when it comes to starting pitchers, given the position's laundry list of injury issues and general unpredictability.

As far as starting pitchers go, though, Montgomery certainly lands on the safer side. He has cleared 155 innings while posting an ERA of 3.83 or better in each of the past three seasons.

He's been even sharper over the past two. In 2022, he set a career-high with 178.1 innings and a career-low 3.48 ERA. Then, he bettered both marks this past season (188.2 innings and a 3.20 ERA) before seeing even better results in the playoffs.

If the Yankees sign Montgomery, they can reasonably expect reliability. And given all of the question marks with this staff, that's something they desperately need.

Montgomery's Cost Shouldn't Be Astronomic

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ARLINGTON, TX - OCTOBER 28: Jordan Montgomery #52 of the Texas Rangers pitches during Game 2 of the 2023 World Series between the Arizona Diamondbacks and the Texas Rangers at Globe Life Field on Saturday, October 28, 2023 in Arlington, Texas. (Photo by Cooper Neill/MLB Photos via Getty Images)
ARLINGTON, TX - OCTOBER 28: Jordan Montgomery #52 of the Texas Rangers pitches during Game 2 of the 2023 World Series between the Arizona Diamondbacks and the Texas Rangers at Globe Life Field on Saturday, October 28, 2023 in Arlington, Texas. (Photo by Cooper Neill/MLB Photos via Getty Images)

Given the way he pitched last season, and the way he elevated that performance on baseball's biggest stage, Montgomery surely once held designs of striking it rich this offseason.

Heyman reported that Montgomery's camp compared him to Aaron Hola, who got a seven-year, $172 million deal from the Philadelphia Phillies. At that price, the Yankees were probably out, especially since they'd be luxury-taxed on every dollar spent.

But Montgomery could be learning what so many other clients of his agent, Scott Boras, have discovered: Most teams aren't interested in handing out blank checks. That's why Cody Bellinger, Matt Chapman and Blake Snell all wound up settling for short-term pacts with opt-outs offering them chances to re-enter free agency as soon as next offseason. Slugger J.D. Martinez couldn't even find that much, despite tallying 33 homers and 103 RBI in just 113 games last season, and wound up with a one-year, $12 million deal with the New York Mets.

It's impossible to know what kind of contract Montgomery would accept, but it's probably safe to assume it won't be as lucrative as whatever had first had in mind. So long as the pay rate is reasonable, the Yankees should pounce, especially since he couldn't sign a qualifying offer and therefore wouldn't include any additional costs, like draft picks or international pool money.

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