‘He Crazy’ — Ex-Raiders Star Makes Feelings Clear on Jon Gruden’s Future After Controversial Exit From Las Vegas

Jon Gruden has been out of football for nearly five years. He resigned as Las Vegas Raiders head coach on October 11, 2021, after The Wall Street Journal and The New York Times published emails he sent between 2011 and 2018 while working as an ESPN analyst, emails that reportedly contained racist, homophobic, and misogynistic language targeting DeMaurice Smith, Roger Goodell, and others.

He walked away from approximately $60 million remaining on a 10-year, $100 million contract. Grudel filed a lawsuit against the NFL, alleging that Goodell personally leaked the emails to force him out, a case now heading to trial in May 2027. The football world has largely moved on, but one player who owes his career to Gruden has not.

Darren Waller Credits Jon Gruden for Saving His NFL Career, Calls for Second Chance

Darren Waller was nobody when Gruden found him. A sixth-round pick by the Baltimore Ravens in 2015, Waller served two NFL suspensions for substance abuse violations before landing on Baltimore’s practice squad in 2018. The Raiders signed him off that practice squad in November of that year, and nobody paid much attention. Then Gruden got hold of him.

In 2019, Waller had 90 receptions for 1,145 yards and three touchdowns. By 2020, he was among the best tight ends in football, setting the Raiders franchise record for single-season receptions with 107, a mark that had belonged to Hall of Famer Tim Brown since 1997.

He earned his first Pro Bowl, finished second among all tight ends in receiving yards at 1,196, and made the kind of jump that does not happen without a coach deliberately engineering it. Waller knows exactly who did that for him.

Appearing on the May 14 edition of the “All the Smoke” podcast, Waller described what the Gruden experience actually looked like from the inside, beginning with something that caught him off guard.

“He led all the offensive install meetings and installed all the plays,” Waller said. “It was literally like a stand-up special, a Netflix comedy special. Just jokes all the time. I remember sitting there a couple of times, and I’m like, ‘Man, he crazy.’ If they ever get these meeting files out in public, he’s canceled. And then the emails hit, and I was like, ‘Oh, sh**.’ But he was hilarious.”

Waller is not minimizing what Gruden’s emails contained, but is distinguishing between the man who showed up at those meetings every day and the man who wrote those words in his private email account over a decade. Those two things apparently co-existed, and Waller is not pretending otherwise.

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What he keeps coming back to is the opportunity. In a league where coaches and front offices frequently talk about player development without delivering it, Gruden actually gave Waller a stage and built an offense around what he could do.

“He loved putting dudes in positions to turn their careers around, and he would give you opportunities,” Waller said. “Like, I wouldn’t have a career. I probably wouldn’t be here today without him giving me the opportunity to show what I got.”

Then Stephen Jackson asked Waller, “Does he [Gruden] deserve another shot?” to which the former Raiders star replied, “I think so.”

Whether the NFL ever allows Gruden back into a coaching role before or after the May 2027 trial is unclear. The Raiders have cycled through quarterback instability since his departure and have yet to recapture the identity Gruden built around Derek Carr and Waller’s chemistry.

However, Tom Brady’s arrival as minority owner and the selection of Fernando Mendoza first overall in the 2026 draft signal a new direction entirely, and Gruden’s era in Las Vegas feels conclusively over.