Time for the Gruden Gamble to pay off?

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Anyone heading to Vegas is taking a gamble. The Raiders took a bit of a gamble leaving Oakland. They an even bigger gamble hiring Jon Gruden. The average tenure of an NFL head coach is just short of four years. Now entering his fourth season as the Raiders head coach the Silver and Black should be seeing a return on their 10 year, $100m investment.

The Raiders will play their first regular season game in Las Vegas with fans on Monday Night Football. Opening their new $1.9Billion stadium fully, the final piece in their long awaited relocation to sin city. The move is no longer an issue, nor the stadium, eyes are starting to turn to the head coach. Jon Gruden enters the fourth of his ten year contract this season and it’s about time the Raiders saw some results.

Now in his second stint with the Raiders Gruden is 114-100 as a head coach. With identical records of 57-55 at both the Raiders and Buccaneers. Image from eastbaytimes.com

Before we look at why the pressure is starting to mount for Gruden, let’s take a look back at his fruitful career in football so far.

The Rise and Fall of Jon Gruden

Flying up with the Eagles

Gruden’s rise up the coaching ranks was impressive. Starting in 1992 at the age of 28 as an offensive assistant in Philladelphia. Quickly being promoted to be the Eagles offensive coordinator after just three seasons. Gruden became the Raiders twelfth head coach in 1998, just six years after starting his professional coaching career.

Over to Oakland

His first stint at the Raiders was pretty successful. Two 8-8 seasons to start, followed by two successive trips to the playoffs on 12-4 and 10-6 records, winning one playoff game each year. In 2002 the Buccaneers did something that in today’s NFL would be seen as ludicrous; they traded two 1st round, two 2nd round picks and $8Million in cash for Gruden in the 2002 off season.

Tampa Time

Tamps Bay’s gamble paid off. Following a 12-4 regular season, Gruden guided the Buccs to their first Super Bowl victory, in his first season. Beating the Raiders (ouch) 48-21 in Super Bowl 37, often referred to as the “Gruden Bowl”. Gruden spent a total seven years at the Buccs, making the playoffs three times. His only playoff victories coming in that first year. Following the 12-4 Super Bowl winning season Gruden went 45-51 with the Buccs and was fired after the 2008 season.

Gruden won the Super Bowl with the Tampa Bay Buccaneers, beating the Raiders 48-21, the year after leaving the Silver and Black. Image from tampabay.com
To TV and back

Following his firing Gruden created the Fired Football Coaches Association. Where he and other out of work coaches could watch and discuss film, players, tactics and all other things coaching. Despite sounding a little desperate the FFCA would end up helping the likes of now Rams head coach Sean McVay, Jags head coach Urban Meyer and former Eagles head coach Chip Kelly.

Alongside the FFCA Gruedn would be appointed ESPN’s colour commentator for Monday Night Football, a roll which he’d excell in for 9 seasons. Before returning to the Raiders as head coach.

Back in Oakland

After nine years out of head coaching the Raiders signed Gruden to a ten yea $100Million contract in 2018. The contract included a no trade clause, hands off Buccaneers! Gruden was tasked with turning the Raiders into a marquee franchise while they made the move 407 miles South East to Las Vegas.

The Raiders have had only one winning season (2016) since the 2003 season. Raiders owner Mark Davis saw Gruden as the man to turn the franchise around.

Gruden’s first two seasons, and the Raiders last in Oakland, weren’t great. 4-12 followed by 7-9, hardly the farewell Oakland deserved. With the Covid Pandemic drastically altering the 2020 season the Raiders started their Las Vegas tenure without fans and without much commotion. Finishing 8-8 and missing out on the playoffs. Now into his fourth season as head coach. It’s time the Raiders saw results.

Gruden the Guru?

Initial success at Philadelphia and winning a Super Bowl in his first season with the Buccs gave Gruden quite the reputation. But has he lived up to the hype? I’d argue no.

He’s now 57-55 (.509) at both the Buccs and Raiders (over both terms). He’s only made the playoffs 5 times in his 14 years as a head coach. His strength, from back in his offensive coordinator/assistant days is his offence. But in his 17 years as head coach and coordinator, he’s had a top 10 offense only 3 times. The last being 1999.

Zigging, Zagging, and who knows what-ing?

Gruden has always been seen as someone who does things their own way, someone who’s not afraid to zigg when everyone zaggs. His gritty, old school attitude works well with the Raiders “Just Win Baby” Mantra, penned by deceased former owner and head coach Al Davis. This willingness to be different can be seen in the Raiders player recruitment history.

There’s been plenty of raised eyebrows at the Raider’s off season activities the past few years. Here’s just a few.


Not afraid of risky signings the Raiders have welcomed players like Richie Incognito, Antonio Brown and Vontaze Burfict to the team. All talented veterans but each with different, controversial pasts. Of those three only Incognito remains, with serial ban-collector Burfict managing 4 games before a season long ban and Antonio Brown never playing a snap in Silver and Black.


The Raiders have also parted ways with some pretty high profile pieces. In the stretch of just over a month and a half, starting September 2018, the Raiders traded away two time All Pro edge rusher Khalil Mack and two time Pro Bowl receiver Amari Cooper, to the Bears and Cowboys respectively. Both were traded for first round picks, Mack for two first rounders plus, which were set to kick start a Raiders rebuild.

Khalil Mack, 2016 Defensive Player of the Year, was traded away. The draft picks received in return have resulted in mixed results. Image from bleacherreport.com

Mack has since gone onto earn himself another All Pro selection and knock his Pro Bowl tally upto six. Cooper has reached over 1000 yards each year in Dallas, no Raiders receiver has done this since Cooper himself. He also has 19 Touchdowns for the Cowboys, 11 more than any Raiders receiver has managed in that time.

Giving up franchise players can an inevitable part of sports. Trading them away can at least bring something in return…

The Draft

There’s no clearer sign of Gruden’s “alternate” approach to football and recruitment than the Raiders last few drafts. 2019, with the two extra picks from the Mack and Cooper trades, was meant to be their draft. With their first pick, number 4 overall, the Raiders selected edge rusher Clelin Ferrell, who many saw going in the 20s. In Ferrells 26 games so far he’s had only 6.5 sacks. The consensus pick pre draft was Josh Allen, who went three picks later t the Jags. Allen has twice as many sacks despite player two fewer games.

The extra picks picked up for Mack and Cooper resulted in Josh Jacobs, Jonathan Abrams and Damon Arnette. Jacobs he’s been a very useful running back, finishing 8th in rushing yards both years he’s been in the league. That can’t be said for Abrams and Arnette, both have played less than 60% of the Raiders games thanks to injuries and haven’t looked great when finally on the field.

Further strange decisions were made in this years draft, selecting Alex Leatherwood with the 17th overall pick, who was rated 75 on our top 100 big board and wasn’t a top 5 offensive tackle prospect in our pre-draft analysis. Time will tell how this works out, but regardless this can be added to the list of odd draft picks during Gruden’s tenure.

What Next?

It’s unlikely the Raiders will move on from Gruden, his ten year contract gives him some wiggle-room. Not that they can’t afford it might I add, the Raiders have more than doubled their value moving to Las Vegas. But the pressure is inevitably on the Raiders to perform this year. More of the same and those voices questioning the Raiders choices will only get louder.

Mediocre results, questionable transactions and questions about Gruden’s ability would be giving any other franchise serious headaches. Entering year four of the Gruden experiment, it’s fair for Raiders management and fans to expect more than another OK season. It’s not easy having the AFC champion Chiefs in your division, but a shot at a wildcard playoff spot should be seen as a given in year four.

It’ll be interesting to see how long of a leash Gruden gets at the Raiders if they fail to make the playoffs this year. If it was another team he may be jobless already.

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