The New York Yankees were linked to many top pitchers during the offseason. Bob Nightengale of USA Today said they put forward a trade proposal to the Chicago White Sox for their 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 out on popular free-agent left-hander Jordan Montgomery, who ultimately accepted a one-year, $25 million deal to join the Arizona Diamondbacks. Now, Jon Heyman of the New York Post has disclosed 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 each year until 2034-41, paid out at $5M per year,” Heyman reported. “My deferral advisor estimated that value at $11.5M per year.”
The New York Yankees’ History With Jordan Montgomery Might Have Ruined Deal
Montgomery has not specified what made the Diamondbacks offer more appealing than one from the Yankees. In a previous report, Heyman wrote that Montgomery was avoiding another suitor, the Boston Red Sox, “because he wants to win,” although on paper the Yankees appear competitive for 2024.
The Yankees and Montgomery also have a history, which might have influenced the pitcher’s decision. He was a starter for the Yankees from 2017 to 2021, with an average 4.01 ERA over 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 show impressive durability since the trade, eventually winning a World Series 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 deserving 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 worth noting that the Yankees were considering a contract for Montgomery with a significant amount deferred. This approach has gained popularity in MLB this offseason, notably with the Los Angeles Dodgers, who successfully completed significant deferred payments for stars like Shohei Ohtani, Teoscar Hernandez and Will Smith.
The Yankees already have substantial salary commitments for the near future. Aaron Judge, Gerrit Cole and Giancarlo Stanton are each owed over $30 million in 2025 alone. The team is already well over the tax penalty thresholds for their 2024 payroll, sitting at more than $306 million.
The team’s consideration of deferred payments would help them avoid further tax penalties while still adding talent, assuming players are open to it. There has been much talk about the team's ability to secure superstar Juan Soto after his one-year contract ends this season. He is expected to command a new deal well in excess of $500 million.
The only feasible way for the Yankees to retain him may be if he is willing to defer some of that money. However, Brittany Ghiroli of The Athletic has reported that Soto may not be open to this.
'He has large eyes,' a source informed her about Soto. 'I believe he's aiming for the same average annual value (AAV) as Ohtani, but without the deferrals,' the source said.The New York Yankees sought to spread out a $72 million deal for free agent pitcher Jordan Montgomery over 17 years, according to a recent report.
