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AL East Notes: Yankees, Montgomery, Red Sox, Clevinger, Shenton

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By Nick Deeds | March 27, 2024 at 11:47pm CDT

Prior to the southpaw signing with the Diamondbacks last night on a one-year deal that guarantees him $25MM, the Yankees were among the teams most frequently connected to Jordan Montgomery this winter as the 31-year-old's former club scouted out potential rotation upgrades in free agency. Reporting connected the sides throughout the offseason and while initial reports indicated that New York was more focused on Blake Snell and Montgomery preferred a return to the Rangers, the sides seemingly reopened negotiations on a hypothetical reunion last week. Per Jon Heyman of the New York Post, however, the sides never got particularly close to a deal before the southpaw landed in Arizona.

Heyman writes that the Yankees remained in talks with Montgomery's agent, Scott Boras, in the days leading up to his deal with the Diamondbacks but that the fourth tier of the luxury tax, which levies a 110% tax rate on spending beyond $297MM, proved to be a major obstacle in negotiations between the sides. While the Yankees suggested a four-year deal to the southpaw's camp (which Heyman indicates may not have reached the "offer" stage of negotiations), the hypothetical pact would have guaranteed Montgomery just $72MM with heavy deferrals that Heyman indicates would have taken the deal's net-present value to just $46MM.

That $11.5MM AAV clocks in at less than half of the $25MM Montgomery will earn in 2024, and the total guarantee over four seasons is less than the $47.5MM Montgomery would be able to earn over two seasons provided he makes at least 18 starts in 2024. While Montgomery was rumored to be searching for a long-term deal even as the calendar flipped to March, it would have been a shock if the left-hander hadn't been able to beat the club's offer elsewhere on the free agent market. With Montgomery now off the table, the Yankees figure to enter the regular season with a starting rotation of Nestor Cortes, Carlos Rodon, Marcus Stroman, Clarke Schmidt, and Luis Gil while ace right-hander Gerrit Cole nurses inflammation in his elbow.

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