Apr 09, 2026
3 min read
Over the past 25 years, the Raiders have been no strangers to dysfunction and Jon Gruden's second stint from 2018 to 2021 was certainly no exception.
Gruden's leaked emails and Henry Ruggs' life-changing car accident were the most devastating headlines of Gruden's second stint with the Raiders, but the way he approached the draft over those four seasons was a fascinating story in itself.
It was no secret that Gruden had complete control over the roster (including the draft) and a report from The Athletic's Zak Keefer shed more light on how Gruden turned three 2019 first-round picks into a disappointment.
According to Keefer, the Raiders used two different draft boards, and Gruden basically did whatever he wanted in the first two rounds of the draft before letting former general manager Mike Mayock take over in the middle and later rounds.
"The Raiders had a ton of top-quality picks in the 2019 draft: three first-round picks and four picks inside the top 40. This should have been the foundation for a rebuild. But it wasn't," Kiefer wrote Thursday.
Kiefer continued: "The Raiders missed out on their first pick and, overall, gambled on Clemson on the edge of Klein Ferrell despite a significant loss in the draft."Panicked In August, the staff began to panic."We had this fourth-rounder out of Eastern Michigan playing every day with the No. 4 pick," one source said.In fact, Crosby, fourth overall, is still the smartest player the Raiders have had in a decade."
"Among those four picks in the top 40, only Josh Jacobs — who Mayock suggested Gruden should come to, according to some in the room — won. By the third day of the draft, the coach's interest had waned. "Gruden wasn't in that category," one source said.
Another disappointing first-round pick for Gruden was Damon Arnett in 2020.
The Raiders were desperate for a cornerback from the 2020 draft, and according to Hondo Carpenter of Sports Illustrated in 2024, Arnette's choice was more on Gruden than Mayock.
"I know, I guess there's close to 10 teams that Damon Arnette doesn't have on his board," Carpenter said on the Las Vegas Raiders Insider podcast two years ago."Mayock isn't Arnett's big guy, but Gruden needs him."
Mayock hasn't talked much (at least publicly) about who was in charge of the Raiders' draft picks while he was there, but he did share an interesting story on Ross Tucker's football podcast a while ago about the biggest lesson he learned during his time as the Raiders GM...
“There's more to it than I ever knew, and it's 24-7 and 365.Football is a tough business anyway, but what I think I've learned more than anything is that even though I'm looking forward to getting out of that building and going to the Jersey Shore for that two-week period in late June, early July, before my wife gets called on the beach.To do Richie Incognito and you have to go back to Vegas to get to that practice if you want to sign him.
You will love the story.I flew back to Vegas.[It was] Tom Cable, our O-line coach, and me and [Jon] Gruden and Cable were going to coach him.Incognito is a 30-year-old former Pro Bowl lineman, you know, and Cable has this little field where it's like a defensive drill that you run back.It is flexible.Checks posture and footwork.Richie makes a circuit.Even minutes.Cable looks at me and Gruden and says, "I've seen enough. Are you okay?"
Chris and I went, 'Yeah, that's great,' and we signed him.I was thinking in my head that I had flown from the Jersey Shore to the beach with my wife to work out in Vegas for a minute to sign Richie Incognito, but that's life. GM It's all day, it's every day... You accept it, I do, and I think everybody's job does. Or it's not for you, it's exhausting, and you'll be exhausted... It's exhausting. But in the end you'll love every second.
Mayock would have been a top notch GM in terms of personnel if Gruden had let him do his job.
