Jon Gruden's Rocky Raiders Tenure, Approach to NFL Draft, FA Detailed by Ex-Staffers in New Report

New details from Jon Gruden's second stint as head coach of the Las Vegas Raiders were revealed in a Thursday report from The Athletic's Zak Keefer.

Gruden, who had previously coached the Oakland Raiders from 1998 to 2001, was hired again by the franchise in 2018.

He went on to lead the Raiders to a 22-32 record over parts of four seasons before he resigned in October 2021 following the New York Times' publication of emails in which he had used homophobic and misogynistic language.

Gruden was working as an ESPN analyst when he was first offered a job by Raiders owner Mark Davis, who ESPN reported was willing to offer Gruden a stake in the franchise that ultimately did not come to fruition.

Keefer's report detailed what Davis' pursuit of Gruden looked like before he signed his head coaching contract, including middle-of-the-night calls and hosting Gruden for visits at team hotels.

One former Raiders executive told Keefer about Davis' bid to hire Gruden, "It was all just so desperate."

Keefer also provided some insight into what Gruden's roster construction techniques looked like once he was installed as head coach.

That included sometimes overriding prospect analysis done by members of the Raiders' scouting team, according to Keefer.

"If he wasn't in on a prospect, former staffers remember, he'd have one of his assistants compile a short video cut-up of the player's worst snaps, then show it to all the scouts," Keefer wrote.

In terms of free agency, two sources told Keefer that Gruden "loved veterans who were All-Pros like eight years ago and were on their way out to pasture" and "anyone who had a name he remembered or had a big game against him in the past."

Gruden would also base his final rulings on free agents on the opinions of his brother Jay Gruden, who at the time was working as head coach of the Washington Redskins, according to Keefer.

Gruden was behind the trades that sent Khalil Mack and Amari Cooper away from the Raiders in 2018, per Keefer.

The Raiders then went into the 2019 draft with three first-round picks, but started out the draft by selecting edge rusher Clelin Ferrell at No. 4.

According to Keefer, there was "considerable pushback" within the Raiders' front office regarding the pick, and the franchise ultimately "panicked" on the clock.

Two of the Raiders' most successful picks in that draft were reportedly made without Gruden's support, according to Keefer.

That included No. 24 pick Josh Jacobs, who Keefer wrote Gruden had to be convinced "to come around on."

Gruden had stopped participating as much in the draft process by Day 3, per Keefer. That's when the Raiders selected Maxx Crosby (fourth round, No. 106 overall) and Hunter Renfrow (fifth round, No. 149 overall).

The Raiders have cycled through four head coaches since Gruden's departure, starting with interim head coach Rich Bisaccia and continuing with Josh McDaniels and Antonio Pierce.

Pete Carroll marks the franchise's latest head coaching departure following his dismissal after the Raiders' 3-14 finish to the 2025 campaign.

The Raiders are now set to start next season with both a new coach in former Seattle Seahawks offensive coordinator Klint Kubiak and the No. 1 pick in the 2026 draft, which the franchise is widely expected to use to select Fernando Mendoza.

Davis and the Raiders will hope those changes are enough to help this team fully recover from the Gruden era by posting their first winning season since 2022 in the near future.