The reasons why Yankees couldn’t sign Jordan Montgomery

When the seasoned southpaw signed a deal with the Diamondbacks on Tuesday, Jordan Montgomery’s protracted free agency finally came to a close. Was he really going to return to the Bronx, though?

Before Montgomery agreed to the one-year, $25 million contract with Arizona, he was the best starting option still available. And the Yankees were reportedly interested in bringing back Scott Boras, while MLB fans waited for him to finalize a deal.

The Yankees were interested in their former starter, but Jim Bowden of The Athletic claims that “their offers required heavy deferrals of 15-20+ years which would have made AAV much less than Diamondbacks offer.”

Since the Yankees’ payroll now exceeds the $297 million upper luxury tax tier, Montgomery’s compensation would be subject to a 110% tax. Deferrals would reduce the luxury tax liability on the deal.

The Yankees selected Montgomery in the 2014 MLB Draft, and he joined the organization in 2017. Before being dealt to the St. Louis Cardinals in 2022 in exchange for outfielder Harrison Bader, he played six seasons in New York. Since then, Montgomery has improved greatly on the mound and shown that he is a trustworthy arm well into the postseason. After being sold to the Rangers at the trade deadline in the previous season, the 31-year-old helped Texas capture its first World Series title by appearing in six postseason games.