Yankees: Jacoby Ellsbury could screw NYY with luxury tax and MLB Draft pick

The New York Yankees‘ work to remain under the luxury tax threshold heading into the 2021 season could end up being all for naught.

Then how bad would the organization look for opting not to spend big to improve the roster while the Los Angeles Dodgers went all out in their effort to repeat as World Series champs, dropping nearly $250 million?

How could this all change for the Yankees? It’s actually pretty fitting.

The worst free agent signing in the history of the franchise — Jacoby Ellsbury — could force the Yankees to go over the tax at some point in 2021. We just don’t know when, which makes it all even worse.

The Bombers did their best Sopranos impression and made Ellsbury disappear after the 2019 season. 

How so? By making the remainder of his seven-year, $153 million contract non-guaranteed after the organization alleged he sought outside, unauthorized medical treatment. Soon after, the MLBPA filed a grievance on behalf of Ellsbury in an effort to recoup the remaining $26 million he was owed.

How could Jacoby Ellsbury ruin the 2021 Yankees’ draft?

But if that grievance ends up being settled in Ellsbury’s favor in 2021, it could really put the Yankees in a bad position. Throw another $26 million onto their 2021 payroll and you have a grand total of … almost $227 million. And that changes a lot of things.

For starters, that will force the Yankees to pay a hefty tax, which was something they were trying to avoid by skimping on roster upgrades. If they have to pay it regardless, they’re going to hear it from the fans, especially if the organization knew it’d be dealing with Ellsbury’s case in the months after free agency.

Additionally, the Yankees will get penalized in whichever MLB Draft proceeds the ruling. If Ellsbury’s grievance ends up with a ruling before the July draft, the Yankees will drop 10 spots, according to MLB.com’s Jim Callis. If it happens after the July draft, it’ll affect their standing next year.

Then again, it’s important to note that information may not be correct. Teams that shoot $40 million past the luxury tax threshold are subject to this draft penalty. The Yankees will only be $16 million beyond the $210 mark if they have to pay Ellsbury this year … unless, of course, there’s more money at stake than we’re currently aware of.

Ellsbury’s 2020 salary was voided by the team. Last year, he was slated to make $21.1 million and also had a $5 million buyout on a 2021 team option, one that the Yankees were 100% going to decline anyway. But that’s a grand total of $26.1 million, and the Yankees’ current payroll is just a shade over $200 million at the moment.

Either way, we’d MUCH rather not be in a position where Ellsbury has another chance to bring this franchise down. And right now, it’s all hanging in the balance.

Maybe if the Yankees get stuck with this cash, they can simply blast past the luxury tax by another $50 million or so midseason? Probably not. Just looking for the upside here, though.

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