Jon Gruden to sign 100 Million/10 Year deal with Raiders

Jon Gruden is Going Back to the Bay Area

At least for two seasons. Then it’s off to Sin City for Gruden and the Silver and Black. 

Regardless of where they are playing, the Raiders have found their guy for the next ten years. As reported by several sources, the Raiders have scheduled a press conference Tuesday and are expected to introduce Gruden as the team’s head coach. The twenty-first head coach in team history, replacing the recently fired Jack Del Rio. It’s been ten years since Gruden roamed the sidelines as an NFL head coach. Furthermore, it’s been twenty years since the late Al Davis introduced a 35-year old Gruden as the Raiders’ twelveth coach in team history. 

Oh how the times have changed for the Raiders. Before the 2002 draft, Al Davis sent Gruden packing to Tampa Bay in a blockbuster trade for several 1st and 2nd round picks. Since the trade, the Raiders have compiled a 92-164 record. Only the Cleveland Browns (77-179) have been worse over that span.


If any non-Raider fan has been on the train over the past 3 seasons, it’s me. I think Derek Carr has the potential to be a perennial MVP candidate, especially with the help of Gruden. They have two stud wide receivers who need someone to light a fire under their ass. Jon Gruden is that guy. To fill the role of offensive coordinator, Gruden has pegged Rams’ QB’s coach, Greg Olson. Olson was the Raiders’ OC during Carr’s rookie season, so there is already some familiarity there. I’m not worried about the offense at all. 

On the other side of the ball, Gruden has chosen Bengals’ DC Paul Guenther to run the defense. Guenther had been apart of the Bengals organization for twelve years. He was the linebackers coach until 2014 when he was promoted to DC. He’ll be tasked with building a fearsome defensive unit around All-World pass rusher Kalil Mack. 

I don’t believe this move instantly makes the Raiders Super Bowl contenders. I’d go as far as saying he doesn’t even make them a playoff team yet, but then I remember how weak the AFC was this season. A few good moves and they’re right back in the thick of things, especially in the AFC West. 

At least Gruden (10 years) and his coordinators (4 years) have time. 

This is where I grow skeptical. 10 years!?!? Really? When has a 10-year deal ever worked out? In the NFL, we’ve never seen anything like this (sounds familiar). The guy has been out of coaching for almost ten seasons. How could you commit that much time and money to something that is more hype and speculation than actual results?

For certain, he’ll get two years in Oakland and two years in Vegas to build a winner. I think he has what it takes. I’m calling it now, the Las Vegas Raiders will win Super Bowl 56.

Gruden’s First Tenure in Silver & Black

In 1997, the Philadelphia Eagles offense ranked in the top 10 in both passing and rushing. Though Philadelphia finished with a 6-9-1 record, the Eagles offensive success caught the eye of Raiders owner/GM Al Davis whose team had finished the season 4-12. By the start of the 1998 season, Gruden was Davis’ guy.


Unfortunately for Gruden, he didn’t have his guy at QB. After the ’97 season, former #1 overall pick (1990) and borderline bust, Jeff George was the incumbent starter in Oakland. Though George was coming off a career season in which he led the NFL in passing yards, Gruden’s offensive scheme was not favorable towards George’s style of play. George came out strong to begin the season, passing for 303 and 270 yards in the first two games. Then the struggles began. In the team’s third and fourth games, George didn’t pass over 200 yards. In the team’s fifth game, George suffered a groin injury. Despite trying to make comebacks in Weeks 9, 12 and 16, George’s season and tenure in Oakland were effectively done. 


Following an 8-8 campaign in ’98, the Raiders went out and signed free agent QB Rich Gannon to run Gruden’s pass-oriented offense. In Gannon’s first season under center in Oakland, the 34-year old set career highs in almost every passing statistic and started all 16 games for the first time in his career. Despite Gannon’s success in the West Coast offense, the Raiders went on to finish 8-8 again. However, all eight losses were by a touchdown or less.


With the turn of the century, so did the Raiders fortunes. Gruden, Gannon, and OC Bill Callahan led the Oakland to a 12-4 record and an AFC West division title. Gannon threw 28 touchdowns to 11 interceptions on way to being name 1st team All-Pro and earning a trip to the Pro Bowl. In the divisional round of the AFC playoffs, the Raiders blew the doors of the Dolphins 27-0 to punch their ticket to the AFC title game. The following week, the Raiders fell to the eventual Super Bowl champions Baltimore Ravens at home 3-16. Rich Gannon was decked early in the 2nd Quarter and was hampered with injury for the rest of the game. Oakland’s chances were doomed.


Expectations were high in Oakland following the 2000 season and the Raiders were ready to match. The Raiders won 10 of their first 13 games. However, late in the season, they fiddled out and their last three games of the regular season. Though they still won the AFC West division title, falling to 10-6 cost the Raiders home-field advantage past the Wild Card Round. In the Wild Card Round, Gannon (23/29, 294 y, 2 TD) and Jerry Rice (9 rec, 183 y, TD) destroyed the Jets in Oakland singlehandedly 38-24.

Since Oakland lost their last three games of the regular season, the Raiders had to travel to New England for the Divisional Round. History has dubbed this game with two names depending on perspective: The Snow Bowl and The Tuck Rule Game. Patriots’ kicker Adam Vinatieri nailed a field goal in a blizzard to tie the game. Then drilled the game-winner in overtime. The game would propel the beginning of the Patriots dynasty. Without knowing it at the time, it also signified the end of an era in Oakland: Jon Gruden’s last game as Raiders’ head man.

The Trade

At the 2002 NFL Draft, Al Davis sent shockwaves through the NFL when he agreed to trade Gruden for two first round picks and two second round picks. 

  • Buccaneers Get
    • (HC) John Gruden
  • Raiders Get
    • 2002 1st Round Pick (21st Overall)
    • 2002 2nd Round Pick (53rd Overall)
    • 2003 1st Round Pick (32nd Overall)
    • 2004 2nd Round Pick (33rd Overall)

The Buccaneers After the Trade

In Tampa, Gruden inherited a 9-7 team that earned an NFC Wild Card berth the previous season. Brad Johnson was the team’s QB coming off a solid 2001 campaign. On the other side of the ball, Monty Kiffin’s defense was one of the best in the league. 

Knowing he had one of the best defensive units in the league, Gruden made it his purpose to elevate Johnson and the offense. In 2002, thats what he did. Brad Johnson had the most efficient season of his 15-year career. Johnson threw 22 touchdowns to only 6 interceptions. 

The Buccaneers went on to finish 12-4 and win the newly aligned NFC South in Gruden’s first season. In the playoffs, the Bucs knocked off San Francisco and took out the Eagles in Philly to earn a trip to the Super Bowl. Super Bowl 37 pitted Gruden’s Bucs against the team the team that traded him. Tampa Bay went on to wipe the floor with the Raiders in route to a 48-21 victory and Gruden’s only Super Bowl ring. 

After the 2002 Super Bowl run, the Buccaneers never quite regained that magic under Gruden. In Gruden’s next six seasons as Bucs head-man, Tampa Bay went 45-51. They finished better than 9-7 once (2005), but won two more NFC South titles (2005, 2007). Over Gruden’s tenure, the Bucs were hit with many salary cap hardships that enabled the team to keep its core nucleus of players intact. 

Tampa Bay lost their last four games of the season in 2008 to finish 9-7 and miss the playoffs. Gruden was subsequently fired after the season. In 2009 he was hired by ESPN and the rest is history. 

The Bucs haven’t made the playoffs since. 

The Raiders After the Trade

Al Davis absolutely got the short end of the stick on this trade. In all fairness to Mr. Davis, Gruden’s contract was up in a year and he could walk for nothing. Hauling in four high draft picks for a head coach was and still is unprecedented. Had the draft picks been allocated better, the move could have gone down as one of the most influential trades in NFL history. Al Davis would have died a genius. 

Draft Woes

At the 2002 NFL Draft, the Raiders used the 21st overall pick they acquired to execute a series of trades that allowed them to trade up to the 17th overall pick. There they selected Phillip Buchanon, an exciting kick returner/cornerback from Miami. Buchanon only played in six games his rookie season. In his first full season of action, he returned two of his six interceptions for touchdowns and returned two punts for scores. After a promising start to his Raiders’ career, Buchanon was sent packing to Houston on draft day 2005 for a 2nd and 3rd round pick. Neither pick garnered much in return. 

With the 53rd pick in the 2002 draft, Oakland selected Langston Walker, a Tackle from California. Walker only started a full season once for the Raiders in his five seasons in Oakland. He subsequently signed with Buffalo in free agency the following season before returning to the Raiders two years later. In 2010, he started 15 games for Oakland in his final NFL season.

Notable Players Passed On in 2002: Ed Reed (24th Overall)

In 2003, Oakland owned Tampa’s 1st round pick. With the last pick in the first round, the Raiders selected Tyler Brayton, a DE from Colorado. Later in the day, they traded away the 2004 second rounder they acquired in the Gruden deal for two more draft picks (LB Sam Williams and WR Ryan Hoag). Neither made an impact in the NFL.

Notable Players Passed On in 2003: Charles Tillman (35th), Jon Stinchcomb (37th), Rashean Mathis (39th), Anquan Boldin (54th), Osi Umenyiora (56th), Robert Mathis (138th)

Notable Players Passed On in 2005: Nick Collins (51st), Vincent Jackson (61st), Frank Gore (65th), Justin Tuck (74th, Evan Mathis (79th), Richie Incognito (81st)


The season after the Gruden trade the Raiders made it to the Super Bowl, but since have only made the playoffs once (2016) in fourteen seasons. In fact, the 2016 season was the only season the Raiders finished above third in their division. Al Davis passed away in 2011 and relinquished control to his son Mark. During the past offseason, Mark Davis announced that the Raiders would be leaving Oakland to relocate to Las Vegas after completion of a new stadium in 2020.


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