Jon Gruden Snarl
Gruden may be past his prime in coaching. (Joe Camporeale/USA TODAY Sports)

Gruden’s First Stint With Raiders

In 1998, Al Davis brought in a young man by the name of Jon Gruden, otherwise known as “Chucky.” At the age of 35 years old, Gruden was to be the head coach of his beloved Raiders. Like Davis, Gruden had a huge personality and wanted things done his way or the highway. Al was all about the vertical passing game, trying to always keep the defense on their toes with speed on the outside threatening to score on any given play. Jon’s offensive plan was based on the West Coast playbook created by the legendary coach Bill Walsh, where he would methodically move the football down the field with shorter passes and the run game. This is where the two would ultimately clash on and off the football field. Gruden would lead the Raiders to back-to-back 8-8 records in the 1998 and 1999 seasons despite butting heads.

Ultimately, the Raiders would break through by winning the AFC West division. They would go on to host the AFC title game in the Coliseum against one of the best all-time defensive teams, the Baltimore Ravens. The Raiders would go on and lose 16-13 in a defensive battle. The following year, the Raiders would find themselves right back in the playoffs. In this game, one of the most controversial plays of all time happened… The “Tuck Rule” against Tom Brady and the Patriots. That offseason, Al Davis had enough of Gruden, and he would go on and trade the Raider captain “Chucky” to the Tampa Bay Buccaneers. That year, Tampa Bay would go on to win the Superbowl against those same Raiders in blow-out fashion.

Gruden To Monday Night Football

After his tenure with the Tampa Bay Buccaneers, Gruden would take his talents to the booth. He would go on to analyze Monday Night games for ESPN. Chucky, with his classic snarl and wild vocabulary, would go on to be one of the most famous/fan-favorite TV personalities. While still working with ESPN, he began his own segment during the NFL offseason. He worked out quarterback draft prospects at “Gruden’s QB Camp.” With all his fame and a great career, Gruden still found himself hungry for more in head coaching. But some would question if he had been away from the game for too long.

Gruden’s Return To The Silver And Black

In 2018, after many rumors of a return to the Raiders, Gruden would finally come home to finish what he had started. Ever since his return, every move he has made has been questionable, especially decisions involving the draft and free agency. Starting with a bang by trading a defensive player of the year and one of the most dominant pass rushers in the league in Khalil Mack to the Chicago Bears for 2 first-round picks. During 2018, Gruden would trade two-time Pro Bowler Amari Cooper to the Cowboys. The Raiders would go 4-12 during Jon’s first season as head coach as he looked to rebuild the franchise.

2019 NFL Draft

Gruden would start the 2019 draft by reaching for a defensive end in Clelin Ferrell at number four overall to “replace” All-Pro Khalil Mack with guys on the board such as Devin White, Devin Bush, and Josh Allen. The Raiders haven’t had a field general in the middle of their defense in the last 20 years, and Jon passed on two. With his second 1st round pick at number 24 overall, the Raiders would go on to select Josh Jacobs from Alabama. He looks like a workhorse back through his first two seasons. Finally, with the 27th overall pick, Gruden would select hard-hitting safety Jonathan Abram, who can’t cover a lick.

After the 2019 season, yet another season with Derek Carr, the Raiders would improve to a whopping 7-9 record. A tremulous offseason due to the Antonio Brown trade. Another questionable decision by the head coach. A few bright spots came out of the 2019 season from Josh Jacobs, Darren Waller, and Maxx Crosby. Jacobs ran over 1,000 yards, Waller solidified himself as a top 3 tight end, and mad Maxx Crosby came off the edge with 10.5 sacks. With that number being a bit inflated, getting 5 of those sacks against the Bengals, who had the worst record in football and started third-round rookie Ryan Finley in his first career start.

In the 2020 draft, The Raiders would take speedster Henry Ruggs III, making him the first wide receiver picked in the 2020 class. Al Davis would have loved this pick. He is looking like Darius Heyward-Bey 2.0. With guys like Justin Jefferson and CeeDee Lamb available, you need a true number 1 receiver instead of a guy you are hoping to become the next Tyreek Hill. Even more suspect, Gruden would reach once again for a second or maybe third-best corner on his own team in college. That was Damon Arnette, who he chose in the first round at 19 overall, from Ohio State.

Another promising start to the season, the Raiders were 6-3 heading into a Sunday night showdown against the rival Chiefs. The Raiders would lose in a shootout against Patrick Mahomes. With that loss, the Raiders would lose 5 of 7 and miss the playoffs once again. That included a blow-out loss to one of the worse teams in the NFL, the Atlanta Falcons, along with other heartbreaking losses against the Chargers and Dolphins. They got no contribution from first-round picks Damon Arnette and Henry Ruggs. Ruggs, who only caught 26 balls all year, was used more as a decoy much of the year.

Gruden 2021 Vision

In offseason four, Jon Gruden is bound to make a splash and finally make a draft pick more based on the upside than need. WRONG!!! Chucky does it again! Stabbing every Raider fan in the heart by picking… ALEX LEATHERWOOD?! WHO?! At number 17, Gruden selects the short-armed offensive guard from Alabama just because he probably “loves football, man.” After completely bombing the entire offensive line, this is how he justifies the pick.

This year, we will see the raiders take a huge step backward. Derek Carr will be running for his life trying to find open receivers in WILLIE SNEED and JOHN BROWN?! This will hopefully be the end of the Jon Gruden era and finally, we will say goodbye to Derek Carr. Once again, tear everything down by starting from scratch like the Raiders have been doing for the past two decades. I know Al Davis is tossing and turning in his grave with disappointment in what Gruden has done. This is not the Raider way, “Just Win, Baby,” seems like it will never come back.

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