MLB Rumors: Details Of Yankees’ ‘Creative’ Pitch To Jordan Montgomery

The New York Yankees really could have used Jordan Montgomery.

Sure, they're not alone in that regard. Montgomery is a very good pitcher. And pitching is very important. But the unpredictability surrounding New York's rotation heading into the 2024 MLB season almost certainly is unsettling for a franchise with World Series aspirations.

So, why didn't the Yankees sign Montgomery, who this week agreed to a one-year, $25 million contract with the Arizona Diamondbacks that includes a vesting option for 2025?

According to Jon Heyman of the New York Post, the Yankees didn't want to enter the fourth tier of the luxury tax, a move that would have significant financial ramifications.

"The issue, as it was with Blake Snell, who went to the Giants, was the fourth-tier, so-called 'Steve Cohen tax,' " Heyman wrote in a piece published Wednesday. "Blame (Yankees owner Hal Steinbrenner) if you will, but that 110 percent tax on teams over the $297M threshold is quite the disincentive for almost all, ironically for probably everyone but Cohen himself (who brought in DH extraordinaire J.D. Martinez late, and will pay that onerous tax.)"

Still, that didn't stop the Yankees from targeting Montgomery, who spent parts of six seasons in pinstripes to begin his MLB career. New York put "serious work" into its Montgomery pursuit and got "very creative" with its planning, per Heyman, in an effort to land the 31-year-old left-hander.

"Their idea was for $72M over four years with $40M of that -- $10M per year deferred for 10-17 years -- that's $5M payments in 2034-41," Heyman wrote. "According to my deferral expert, the Yankees' idea would have been worth about $46M in net present value -- or $11.5M per year for Montgomery (and cost the Yankees $24.15M per).

"With $10M a year deferred, Montgomery would take three years to pocket $24M when he's getting $25M for one in Arizona."

All told, it's easy to see why Montgomery chose the Diamondbacks' offer, which includes a second-year option that reportedly will vest at $20 million if he makes 10 starts in 2024 (and an additional $2.5 million added if he makes 18 or 23 starts).

The deal falls short of the six-figure payday that Montgomery and his agent, Scott Boras, probably expected at the beginning of the MLB offseason, when the veteran southpaw was widely considered one of the top free agents available. But it still trumps what the Yankees seemingly were willing to bring to the table while solidifying their rotation for 2024.