Getty The New York Yankees and general manager Brian Cashman offered Jordan Montgomery a heavily-deferred contract, according to a new report.
The New York Yankees were tied to several premier pitchers during the offseason, with Bob Nightengale of USA Today reporting that they made a trade proposal to the Chicago White Sox for ace Dylan Cease and a $150 million offer to former free agent Blake Snell.
Neither pitcher ended up joining the Yankees and the team also missed on coveted free-agent southpaw Jordan Montgomery, who ultimately took a one-year, $25 million to join the Arizona Diamondbacks. And now, Jon Heyman of the New York Post, has revealed the specific offer that the Yankees had in mind for Montgomery.
“The Yankees’ idea was to give Monty $72M for four years with $10M deferred a year until 2034-41, paid out at $5M per year,” Heyman reported. “My deferral guru pegged that value as $11.5M a year.”
The New York Yankees’ History With Jordan Montgomery Might Have Scuttled Deal
Montgomery hasn’t outlined specifically what about the Diamondbacks deal was more enticing than an offer from the Yankees. In a previous report, Heyman wrote that Montgomery was avoiding another suitor, the Boston Red Sox, “because he wants to win,” though on paper the Yankees seem competitive for 2024.
The Yankees and Montgomery also have a history, which might have been part of the pitcher’s calculus. He was a starter for the Yankees from 2017 to 2021, averaging a 4.01 ERA across 388 innings. He made three more starts for the Yankees in 2022 before being traded for relatively little value in the middle of the season.
Montgomery went on to improve and demonstrate impressive durability since the trade, ultimately winning a World Series championship with the Texas Rangers last season.
“It’s possible the soft-spoken left-hander is still upset that (general manager Brian) Cashman didn’t think he was worthy of a postseason start in 2022, choosing instead to trade him to the Cardinals for center fielder Harrison Bader,” Randy Miller reported for NJ.com.
The New York Yankees Seem to Be Interested in Deferring New Contract Salaries
It’s also notable that the Yankees were exploring a deferral-heavy contract for Montgomery. That structure has gained momentum in MLB this offseason, led by the Los Angeles Dodgers, who were able to complete the sport’s most aggressive offseason by deferring millions of contract dollars for stars like Shohei Ohtani, Teoscar Hernandez and Will Smith.
The Yankees already have a lot of salary on the books for the near future. Aaron Judge, Gerrit Cole and Giancarlo Stanton are each owed more than $30 million in 2025 alone. And the team is already well within the tax penalty tiers for their 2024 payroll at more than $306 million.
The team’s interest in deferrals, however, would allow it to avoid even more tax penalties while still adding talent, assuming players are amenable. Much has been made about the team’s ability to lock in superstar Juan Soto after his one year contract is up at the end of the season. He’s expected to command a new deal well into the $500 million range.
It could be that the Yankees’ only real shot of retaining him would be if he’s willing to defer some of that money. However, Brittany Ghiroli of The Athletic has reported Soto may not be open to that.
“He’s got big eyes,” a source told her of Soto. “I think he’s after the AAV (average annual value) Ohtani has, without the deferrals.”