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How much will the Raiders ultimately pay Jon Gruden to leave? It depends if he wants to fight

·NFL columnist
·5 min read
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Amid the pomp and splendor of Jon Gruden's news conference when he returned to the Raiders in 2018, the jaw-dropping megadeal was never far from the stage. In one chair sat team owner Mark Davis in a silver-gray pinstriped suit, emotionally exhaling about his dream becoming reality. Next to him, a beaming Gruden sat with a black and silver tie, thanking Davis from the bottom of his heart.

The spoken bond between them was a shared vision of the future. The unspoken bond, the one that had the entire NFL buzzing, was the 10-year, $100 million contract delivered to Gruden to guide that vision.

“Raider Nation, this is a big effing deal,” Davis said that day.

“If I can’t get it done, I’m not going to take their money,” Gruden later told USA Today.

Well, here we are nearly four years later. The Mark Davis dream became reality and now nightmare. And the bottom of Gruden’s heart has nothing to give these days other than apologies to the offended. But the bond of that Raider For Life contract still grips the franchise, even when the team is figuratively ablaze and the bonds between team owner and coach have been broken.

Somewhere in all of this, Davis still owes Gruden a lot of guaranteed money for the remaining six years of his contract. This despite Gruden stepping down last week amid a storm of controversy over racial, anti-gay and misogynistic emails he exchanged with former Washington Football Team executive Bruce Allen. How much money exactly is a matter of debate.

OAKLAND, CA - AUGUST 10:  Head coach Jon Gruden (L) and Owner Mark Davis (R) of the Oakland Raiders talking with each other while looking on as their team warms up prior to the start of a preseason NFL football game against the Detroit Lions at Oakland Alameda Coliseum on August 10, 2018 in Oakland, California.  (Photo by Thearon W. Henderson/Getty Images)
In happier times, Jon Gruden and Raiders owner Mark Davis share a moment in 2018, the year the Silver and Black re-hired Gruden to lead the team as head coach. (Thearon W. Henderson/Getty Images)

NFL Network reported Sunday that Gruden is still owed “about $40 million over five years of his contract” and that the two sides will work on a settlement despite Gruden having resigned his position. The implication of Gruden still being owed money after resigning appears to indicate that the resignation came under some form of duress that would ultimately entitle him to a golden parachute.

How much of the $40 million is Davis willing to pay Gruden and how hard does the former coach want to fight for it? A source close to the coach told Yahoo Sports that some of Gruden's confidants have suggested he explore whether he might have legal grounds to engage the NFL for damages, given that his identity in the emails was ultimately leaked by a person with intimate knowledge of the league’s investigation into the workplace culture of the Washington Football Team. However, the source added that Gruden and Davis appear to be taking a path toward an amicable settlement rather than a punitive legal battle between the two men or Gruden and the NFL.

The fact that after just over three seasons of work Gruden would be owed only $40 million of his supposed $100 million deal is highly suggestive of two things that circled around the league’s contract community in 2018: First, that the entirety of Gruden’s $100 million deal was not fully guaranteed, making it similar to the player contracts that are often inflated with voidable or non-guaranteed cash; and second, Gruden’s deal was likely backloaded, meaning that, no, he didn’t make $60 million in his first three-plus seasons and then become a bargain in the remainder of the 10-year deal.

Why is Gruden still owed any money if he resigned? The legalese is called "constructive discharge," which is the act of resigning under the pressure of a firing. Essentially, if Davis told Gruden that he would either be fired or could resign under duress, it would be considered constructive discharge. And if Gruden’s legal representation can argue that the Raiders didn’t have grounds to force a Gruden resignation over emails that pre-dated his employment then Gruden can still be entitled to whatever guaranteed money was left on his deal.

The way it has stacked up, this appears to be precisely what happened. And the whole legal argument about what right the Raiders had to fire Gruden for cause all depends on what is written into his contract. What really matters is whether Davis wants to pay Gruden that guaranteed money, and whether Gruden wants to raise a legal fight about it. At the moment, it appears both sides want to work out a settlement and part ways as quietly as possible rather than turning this into the second (and far less appealing) Davis and Gruden center-stage spectacle of the past four years.

It’s a heck of a place to end up less than four years after exchanging heartfelt gratitude and sharing visions of dreams about where this would all go. It’s also a tale about what can happen when a team signs any coach to a 10-year contract with massive sums of guaranteed money anchored into it. Davis was right, this was a big effing deal. Both on the way in and on the way out.

And while Gruden didn’t get it done with the Raiders, there’s still money for the taking if he wants it. One more set of chairs waiting for the two men, signing one last check before spending the rest of their days figuring out what both might have cost themselves inside this busted reunion.

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