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Jeffrey Lurie avoided Jon Gruden. The Eagles’ owner had reasons. | Marcus Hayes

Once a bright and eager coaching mind, Gruden turned into a caricature of himself after success in Oakland, Tampa Bay, and ESPN, and his racism, sexism, and homophobia have now cost him his career.

Disgraced former Raiders head coach Jon Gruden is out of the league after his resignation following the emergence of racist, sexist, and homophobic emails.
Disgraced former Raiders head coach Jon Gruden is out of the league after his resignation following the emergence of racist, sexist, and homophobic emails.Read moreJohn Locher / AP

Years ago, Jon Gruden pulled me into the steamy shower room at old Texas Stadium, which was empty of any Eagles players, and put his hand on my shoulder.

“Look,” he said, his piercing blue eyes staring hard at mine. “I just want a quarterback who can win games. And we both know who can win games.” And then he walked out.

In those few words, Gruden was telling me he’d seen enough of Ty Detmer, who is white, and wanted to replace him with Rodney Peete, who is Black. This was 1997, when being a Black quarterback in the NFL was still relatively unusual. Gruden didn’t seem to care what color his quarterback was.

That was then.

On Monday, Gruden resigned from his $10 million-a-year head-coaching job with the Las Vegas Raiders after a trove of racist, homophobic, and misogynistic emails were uncovered over the past week. The emails also criticized the NFL’s reforms over concussion protocol and its social justice initiatives, and routinely referred to commissioner Roger Goodell with a homophobic slur. Many of the emails were exchanges with his longtime running buddy, former Raiders, Bucs, and Washington executive Bruce Allen.

» READ MORE: Jon Gruden resigns as Raiders coach over racist, misogynistic, and homophobic e-mails

It was almost as stupid as it was offensive. At any rate, Gruden will never work in football again.

I’m a little surprised. This is not the Jon Gruden I thought I knew. But perhaps the Eagles knew Jon Gruden had changed; maybe not that he’d become the embodiment of good ol’ boy oppression, but that his character had warped into something they did not want to be the face and voice of their franchise. Jeffrey Lurie knew something.

That’s why Lurie never courted him in his coaching searches in 2013 and 2016, two league sources who formerly worked for the Eagles confirmed Tuesday. In fact, while those searches were happening, the sources told me — completely off the record, at the time — that Lurie would never employ Jon Gruden. They got that one right; coincidentally, Gruden sent the offensive messages from 2011-18.

One of those sources even predicted quick failure when the Raiders hired Gruden in 2018. I woke up to this text message Tuesday morning:

“Told you so.”

Lurie has stayed in touch with Gruden for the past two decades, but the relationship never became very personal. They are vastly dissimilar people.

Lurie is about as close to a progressive as an NFL owner gets; long before the Woke movement existed Lurie hired openly gay executives, female executives, Black coaches and general managers, and championed the careers of Donovan McNabb and Michael Vick.

From coach to cretin

In 1997, Gruden wasn’t Chucky; he was “Gru-Dog,” a nickname Peete gave him; a bright, innovative young coordinator whose inexperience caused some to question his credentials, but whose energy and honesty won over players like Peete, the team’s clear leader, and stars like running back Ricky Watters and Irving Fryar, all of whom are Black.

Back then, the Eagles were more diverse than any NFL organization. Gruden worked for a Black head coach, Ray Rhodes, whom he apparently respected and adored. Gruden worked alongside a Black defensive coordinator, Emmitt Thomas, whose coaching abilities impressed him and whose accomplishments awed him: Thomas’ five Pro Bowls and 58 interceptions finally landed him in the Pro Football Hall of Fame in 2008. Gruden worked with player personnel men Dick Daniels and John Wooten, both of whom are Black.

At the end of the 1997 season the Raiders hired Gruden, who was just 34, over a 45-year-old Jets defensive coordinator named Bill Belichick. Gruden wore a black chalk-stripe suit to his introductory news conference. He bragged that former Eagles quarterback Randall Cunningham, who is Black, and whom Gruden called a good friend, gave him that suit.

This was when Gruden was a brilliant young strategist, a demanding teacher, a ferocious competitor, and ravenous for success. Sure, he was sometimes crass and brutish, and sometimes even rude, but so were many NFL coaches, including Black ones. I remember thinking:

“Gruden’s kind of a wacko, and a boor — at least he’s not a racist.”

Yes. Well.


By the time Gruden connected with Rich Gannon in Oakland in 1999, there were signs he’d begun to admire his own genius. Gannon was an athletic journeyman who, in his three seasons with Gruden, threw for more than 11,000 yards and 79 touchdowns as Gruden turned the Raiders into a playoff team. The cameras loved Gruden, a photogenic, wispy blond with sharp features and those icy eyes. When Raiders running back Harvey Williams compared Gruden’s angry face to the homicidal doll featured in the “Child’s Play” movie franchise, it stuck.

At first, the nickname embarrassed Gruden. But by the time Gruden lost to Belichick and the Patriots in the AFC playoffs after the 2001 season, he’d become a star.

Gruden’s success with Gannon and the Raiders convinced the Buccaneers to send two first-round picks, two second-round picks, and $8 million cash to Oakland to buy out the last year of Gruden’s contract in early 2002 (Raiders owner Al Davis didn’t want to spend big money to re-sign Gruden.)

At that point, Gruden had begun mugging Chucky poses for the sideline cameras. This continued in Tampa Bay, where he won a Super Bowl that first season, making him, at 39, the youngest coach to ever win it. What’s more, Gruden had beaten the Raiders, the team he’d built, and the team that declined to pay him what he thought he was worth.

When I saw Gruden in a hotel bar at a Super Bowl two years later, the hubris was palpable. He was changing.

Chucky personified

Gruden hooked up with Allen in Tampa in 2003. Between them, they’d run the franchise into the ground by 2008, after which Gruden was fired. Once known as a player’s coach, Gruden had drawn the ire of many Bucs players, with several ripping him to the media. (Former Bucs defender Simeon Rice called him a “scumbag.”)

Jon Gruden had become a caricature of himself.

Chucky will be back and hopefully my teeth will be as sharp as ever,” he told

Not so fast. Nobody wanted him or his teeth. He became less desirable as the years went on, but, oddly, he’d become more visible — as a broadcaster.

Two former ESPN employees say that when Gruden landed at ESPN in 2009 as their “Monday Night Football” analyst, he was eager to contribute and educate, a good teammate. By the time he was featured in a show called Gruden’s QB Camp, where he grilled NFL prospects before the 2012 draft, he’d become infatuated with his TV fame and his nickname; he actually had a Chucky doll on his shelf where viewers could see it. Just before the 2012 season he signed an extension with ESPN, then another in 2014 that, at $6.5 million per year, made him the highest-paid member of ESPN’s talent stable, and completely insufferable, according to the two former ESPN employees.

The sources said the network was not sad to see Gruden go when Mark Davis, Al’s son, gave Gruden a 10-year, $100 million contract to return to coaching.

Who is this guy?

The last time I saw Jon Gruden, he’d just beaten Frank Reich in Indianapolis in the fall of 2019, and he was ... different. Bitter. Hard.

He should have been happy. It was a road win, accomplished despite having the NFL’s dirtiest player, Raiders linebacker Vontaze Burfict, ejected for drilling Jack Doyle with a head shot in the second quarter. Gruden wasn’t happy. He was ... different.

I walked over and tried to say hello to him after his postgame press conference. He ignored my efforts. I’d heard he’d become this kind of guy — indifferent to you unless you were of some use to him — and yes, he’d always been that guy, to some degree. But this was ... different.

You saw that same cold, indifferent guy after the Raiders lost to the visiting Bears on Sunday, as Gruden answered questions regarding the first reports, from the Wall Street Journal, about an email in which Gruden used a racial trope to mock NFLPA chief DeMaurice Smith’s lips. He was defiant, apologizing unapologetically, and seemed likely to survive the controversy. After all, the NFL is the NFL, and it was just a little racism, and we all know how tolerant the NFL can be of that particular cauldron of evil.

Gruden told The Athletic that “I have never had a blade of racism in me.”

As it turned out, it wasn’t one blade. It was a big backyard full of racist, sexist, homophobic thoughts, opinions, and offensive beliefs.

This is a guy who can never return to coaching in a league in which 70% of the players are Black; in which women coach, scout, and act as principal owners; in which Carl Nassib, a Raiders defensive end, announced in June that he was gay, becoming the first openly gay active NFL player. All the kind words Gruden said at the time now appear as false as his initial apology.

How is this guy going to coach an openly gay player?

This was not the same guy who once shared his true thoughts about player quality in that shower room. This was a very changed man.

And Jeffrey Lurie knew.