Inside Jon Gruden’s disastrous second run with the Raiders
Mark Davis’s six‑year, 15‑flight pursuit of Jon Gruden culminated in a 10‑year, $100 million contract that promised to revive “The Raider Way.” The owner’s optimism was palpable at the 2018 introductory press conference, where he declared the hire “the biggest day of my life.”
Gruden first rose to prominence in Oakland from 1998 to 2001, transforming the franchise into a playoff contender with a high‑octane offense. He left after the 2001 season when Al Davis traded him to Tampa Bay for two first‑round picks, two second‑round picks and $8 million.
In Tampa Bay, Gruden coached the Buccaneers to a Super Bowl XXXVII victory over his former Raiders, but the team failed to win a playoff game in the six seasons that followed. After a nine‑year stint as an ESPN analyst, his name resurfaced on multiple owners’ shortlists, including Indianapolis and a potential executive role with Peyton Manning.
When the Raiders fell from 6‑6 to 6‑10 under Jack Del Rio in 2017, Davis intensified his courtship, often calling Gruden late at night or before kickoff. A staffer witnessed the two in a hotel elevator the night before a Week 16 loss, a game Gruden would later call from the ESPN booth.
Gruden eventually agreed to return, after consulting his wife and mother and making numerous trips to Tampa where Davis had a favorite hotel and laundromat. The owner’s grin at the press conference lasted the full 37‑minute introduction, as he proclaimed, “Once a Raider, always a Raider.”
At the time of Gruden’s return, the Raiders were poised to draft Heisman winner Fernando Mendoza with the 2026 top pick, and NFL legend Tom Brady had bought a minority stake in the team. New head coach Klint Kubiak, fresh from a Seahawks Super Bowl run, and defensive anchor Maxx Crosby were also on the roster.
Gruden’s authority was immediate and absolute; scouting trips and senior‑bowls could be dismissed in minutes by his “kill tapes.” Staff recalled that if Gruden was not involved in a prospect evaluation, an assistant would assemble a video of the player’s worst snaps and present it to the scouts.
One former employee described the process: “You can make a player look any way you want. You can make Tom Brady look like a bum.” The kill‑tape culture silenced dissent, especially from younger personnel staff who feared losing their jobs.
Gruden’s relationship with General Manager Reggie McKenzie quickly soured, with Gruden dismissing any potential conflict by saying, “Reggie will win a lot of ’em, he’s a lot bigger than me.” Within a year, McKenzie was replaced by former NFL Network analyst Mike Mayock, a first‑time GM with no prior front‑office experience.
Mayock’s appointment signaled that Gruden intended to control roster construction; a former employee noted, “When you see an established coach bring in a GM who’s never done the job, it’s 100 percent because the coach wants to run the building.”
Mayock’s first major personnel decision illustrated Gruden’s influence: an experienced analyst was told, “Jon heard analytics in your title and wanted nothing to do with you,” after which the interview was canceled. The Raiders finished fifth in the league in challenge success rate that season but went 1‑for‑10 on coach’s challenges in 2019.
Gruden’s roster philosophy favored veteran All‑Pros on the decline, often those he remembered from past games. Scouts reported that when a veteran became available, Gruden would intervene, sometimes overruling weeks of scouting work in a matter of minutes.
Defensive coordinator Paul Guenther recounted a pivotal moment when Gruden asked whether to extend the team’s best defensive player or re‑sign five serviceable starters. Guenther replied, “I took this job to coach Khalil Mack,” only to learn that Gruden had traded Mack for two first‑round picks.
“We let five starters walk out the door, and now Khalil’s gone?” Guenther asked, highlighting the chaotic roster management. The Raiders gave up the most points in the league that season, a direct result of losing their defensive cornerstone.
In 2019, Gruden also traded wideout Amari Cooper to Dallas, accumulating three first‑round picks and a fourth‑rounder inside the top 40 for the draft. The plan was to rebuild with premium picks, but the execution faltered.
The fourth‑overall selection, edge rusher Clelin Ferrell, was chosen despite internal pushback and a plan to trade back for a later pick. By contrast, a fourth‑rounder from Eastern Michigan outperformed Ferrell in subsequent practices, underscoring the draft mis‑evaluation.
Only two of the top‑40 picks proved valuable: defensive end Maxx Crosby, a fourth‑round steal, and running back Josh Jacobs, who Mayock persuaded Gruden to draft. The rest, including tight end Foster Moreau and wideout Hunter Renfrow, arrived later in the draft and offered modest contributions.
Antonio Brown’s 2019 arrival epitomized the cultural chaos; he arrived by helicopter, missed most practices, and clashed with staff, culminating in a release before playing a regular‑season snap. Mayock later said, “I don’t think that guy ever intended on playing football for us,” reflecting the lack of character assessment.
Gruden’s tendency to overlook character flaws was evident in multiple free‑agent signings, where personal issues were ignored in favor of name recognition. This pattern contributed to a roster lacking cohesion and depth.
Owner Mark Davis remained largely hands‑off, often unaware of personnel decisions, a stark contrast to his father Al Davis’s hands‑on approach. Former employees described Davis as “a fan” who did not understand modern NFL operations.
Mayock, despite his scouting reputation, struggled with the GM role, relying heavily on director of pro personnel Dwayne Joseph. Scouts praised Mayock’s respect for their work, yet his inexperience in front‑office mechanics was evident.
The dual‑draft‑board system that emerged in Las Vegas—one led by Gruden and coaches, the other by Mayock and scouts—created confusion and inefficiency. One insider said, “I’ve never heard of a team having two draft boards; there’s no way we’re gonna survive this.”
In the 2020 draft, Gruden allowed offensive line coach Tom Cable to sway the selection of Alabama tackle Alex Leatherwood at 17th overall; Leatherwood was cut before his second season. By the time Gruden resigned in 2021, the Raiders’ roster was depleted of homegrown talent.
Gruden’s resignation followed the New York Times revelation of racist and misogynistic emails he sent while at ESPN. He later sued the NFL, alleging intentional leaks, with a trial scheduled for May 2027.
Interim head coach Rich Bisaccia led the team to a 4‑0 finish and a playoff berth, the franchise’s second since 2002, before a wild‑card loss to Cincinnati. Mayock’s attempt to remove Bisaccia’s interim tag was rebuffed, and both were dismissed.
The following table summarizes Raiders leadership, coaching, and GM records from 2017 through 2026.
| Season | Coach | GM | Record | AFC West Finish |
|---|---|---|---|---|
| 2017 | Del Rio | McKenzie | 6‑10 | 3rd |
| 2018 | Gruden | McKenzie | 4‑12 | 4th |
| 2019 | Gruden | Mayock | 7‑9 | 3rd |
| 2020 | Gruden | Mayock | 8‑8 | 2nd |
| 2021 | Gruden/Bisaccia | Mayock | 10‑7 | 2nd |
| 2022 | McDaniels | Ziegler | 6‑11 | 3rd |
| 2023 | McDaniels/Pierce | Ziegler/Kelly | 8‑9 | 2nd |
| 2024 | Pierce | Telesco | 4‑13 | 4th |
| 2025 | Carroll | Spytek | 3‑14 | 4th |
| 2026 | Kubiak | Spytek | — | — |
By 2022, the Raiders had moved to a new Las Vegas facility, physically separating coaches from scouts per an Al Davis maxim to prevent “buddying up.” This structural division reinforced the dual‑board dilemma.
The 2021 draft further exposed the chaos; Gruden allowed the selection of Alabama tackle Alex Leatherwood, who never contributed, while Mayock’s later picks—Crosby, Moreau, Renfrow—provided the only tangible returns. The lack of alignment between coaching and scouting hampered roster development.
Free‑agency missteps continued, highlighted by the trade of Khalil Mack and the failed acquisition of Antonio Brown, both of which reflected Gruden’s overreliance on name recognition over character. These moves contributed to a talent vacuum that persisted through 2023.
Legal troubles compounded the on‑field issues: first‑round pick Henry Ruggs III was sentenced to prison after a fatal high‑speed crash, and first‑rounder Damon Arnette was released following a weapons‑related video. Both incidents removed high‑profile players from the roster.
The 2020 draft class dissolved rapidly; four of the first five picks were off the team within 18 months, leaving the Raiders without a solid young core. The combination of draft busts and off‑field scandals eroded any momentum the franchise hoped to build.
Mayock’s tenure as GM ended after the 2025 season, and John Spytek took over, allocating $281.5 million in contracts during the 2026 free‑agency wave. Despite the spending, the team’s core remained thin, relying heavily on the anticipated impact of Fernando Mendoza.
Analysts note that the Raiders’ pattern of allowing high‑profile coaches to dominate personnel decisions mirrors earlier eras, where owners like Mark Davis “let you do your thing” without substantial oversight. This approach has repeatedly resulted in fragmented decision‑making.
Tom Brady’s minority ownership, acquired in 2024, adds another layer of influence, with reports that he will have a say in football decisions. The synergy—or lack thereof—between Brady’s vision and the front office remains uncertain.
Looking ahead, the Raiders face a pivotal moment: whether the combination of a top draft pick, increased financial investment, and a new coaching staff can finally align the organization’s strategic direction. The franchise’s history suggests that without clear, unified leadership, optimism alone will not translate to success.
