MLB insider reveals what every Yankees fan was thinking about Jordan Montgomery talks

When the Arizona Diamondbacks signed Jordan Montgomery to a one-year, $25 million contract (with a weird option plus incentives?), many fans were wondering why their team didn't make that happen. Turns out, Monty wanted a smaller market team that was in contention. Easy enough.

But for the New York Yankees, as we said countless times this offseason, signing Monty was never going to happen, regardless of what the "interest" levels were. The Yanks had every reason to remain involved, but that didn't mean they were the most likely landing spot.

First and foremost, the Yankees betrayed the left-hander back in 2022 when they blindsided him with a trade to St. Louis, and then insulted him on the way out by saying he wasn't going to be a playoff starter for them. A year later, Montgomery was the Rangers' most important starter en route to a World Series victory.

Not only that, he was misutilized in New York. Upon his arrival to St. Louis, pitching coach Mike Maddux (who then joined the Rangers before Monty was traded there last year) revamped the left-hander's offering to improve his approach. The results were immediate and Montgomery had never seen more success.

And then there was the elephant in the room some fans didn't care to address: the luxury tax. Every dollar the Yankees spend from this point forward is taxed at a 110% rate, meaning a $25 million contract for Monty would've cost them over $50 million for 2024.

MLB insider reveals what every Yankees fan was thinking about Jordan Montgomery talks

As expected, per Jon Heyman of the New York Post, the two sides "never got traction or even close to traction."

Heyman noted the Steve Cohen tax threshold being the main culprit and added "there's no evidence any official offers were presented." Also, as predicted, the Yankees were unsure if Montgomery even wanted to return, which would've been very important information to know before diving into these waters!

According to Heyman's intel, Montgomery's camp did engage with New York, but requested shorter-term deals with higher AAVs -- something the Yankees couldn't make happen because of the luxury tax. Instead, they countered with a very unappealing set of offers.

"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. 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.

"And he would take until 2041 — when he’s 48 — to match what he’s getting in Arizona in two years, assuming he vests the second year with 23 starts and earns the full $50M."

Did you think for a second that Montgomery was going to play by the Yankees' financial restrictions after the way he was treated? If he was returning, it was going to be on his terms, especially after finishing on a high note in a contract year. He made his choice, and now we can stop speculating on something that was nothing but a waste of time for fans' hopes.