Since that tragic loss to the Tampa Bay Buccaneers in Super Bowl XXXVII, the Oakland Raiders have been a franchise in free fall.

In the six seasons since Chucky exacted his revenge on Al Davis, the Raiders have won just 24 games while losing 72 contests along the way.

Here are the 10 worst moments of those last six years.

10. Drafting Michael Huff –While the jury is still out on JaMarcus Russell, Darren McFadden and now Darrius Heyward-Bey, it would appear that the ruling on Michael Huff is a unanimous choice to give his Raider career the death penalty. Huff Daddy was the 7th pick in the 2006 draft, a draft that might go down as the biggest collection of busts this side of Dolly Parton and a pre-op Soliel Moon Frye. After being benched halfway through his third year in the NFL, the Raiders drafted a virtual unknown safety by the name of Michael Mitchell to replace him. Huff has recorded just one interception, one sack and one safety in 39 career starts.

9. Joe Flacco’s Demolition of Oakland – In week 8 of the 2008 season, the Baltimore Ravens took apart the Raiders to the tune of 29-10. That afternoon, the Raider defense made rookie Joe Flacco look like Joe Montana. Flacco threw a 70-yard TD in the first quarter, ran for a TD from 12 yards out in the fourth quarter and to add insult to injury, Flacco burned linebacker Ricky Brown for a 43-yard reception as well.

8. The 2008 Raider Free Agency Class – Few franchises have shown such poor personnel decisions in a decade as the Raiders did in just one summer. Last year, Al Davis committed $70 million to DeAngelo Hall, $55 million to Javon Walker, $39 million to Gibril Wilson and $16 million to Kwame Harris. Hall played opposite Nnamdi Asomugha and got undressed more often than Vida Guerra. The Raiders severed ties with MeAngelo just 8 games into a 7-year deal. Wilson and Harris were both let go just one year after signing multiyear contracts. Meanwhile, Walker caught a grand total of 15 passes in ’08 then needed season ending ankle surgery and is now attempting to comeback from a secret knee surgery he had during the offseason.

7. Sebastian Janikowski’s Fake Field Goal – If you met Sebastian Janikowski on the street, you most likely would think he’s either a construction worker or a bouncer for a Ukrainian night club. As Tom Cable learned the hard way, it just won’t end well when you try to give the ball to a 260 pound kicker who runs a 7.5 second 40-yard dash. A winnable game against the Kansas City Chiefs became a 20-13 loss thanks in large part to Cable’s gutsy yet misguided effort to fool everyone in the stadium including his own team.

6. Tyler Brayton knees Jeremy Stevens in the “man region” – Losing 16-0 on Monday Night Football and allowing 9 sacks is embarrassing. Losing your cool and kneeing an opponent in the package – even if that opponent is as dirty as Borat’s bed sheets – is reason to stop watching football all together. It still amazes me that the Raiders won two games in 2006. That ’06 team will forever be remembered as the worst offense in NFL history and for Tyler Brayton giving Seahawk tight end Jeremy Stevens a friendly reminder of where the Raider stereotypes come from.

5. Opening Night Losses on National Television – The start of each season brings the hope of a new day. If you’re a Raider fan, the start of each of the last six seasons has been a reminder of just how much liquor you’ll need to make it to the New Year. Twice in the last three years the Raiders have opened the season in primetime on Monday Night and they’ve lost those two games by a combined score of 68-14. The Chargers rolled the Raiders in a Monday Night sack fest in 2006 to the tune of 27-0. Then Jay Cutler, rookie Eddie Royal and every player in a Bronco jersey picked on DeAngelo Hall in route to a 41-14 loss on the ’08 Monday Night debacle. History is against us, but the Raiders and Chargers will again be on Monday Night to open the 2009 season. Let’s hope that Tom Cable plants a few land mines on the Charger sideline for that night.

4. Rehiring Art Shell – Al Davis had an Uncle Rico moment in 2006 when he tried to relive his football past. Davis turned back the clock to 1990 and rehired Art Shell. Shell’s stoic sideline glare became the face of ineptitude. As if the Art Shell move wasn’t bad enough, the Raiders topped themselves by resurrecting the career of offensive coordinator Tom Walsh. Walsh was out of pro football for more than a decade and had been running a bed and breakfast in Idaho. Walsh’s dubious contribution to the NFL record books was to place Randy Moss in the annals as having played for not only the highest scoring offenses in football history but also as a member of one of the worst ever. Walsh’s offense tallied just 168 points in 2006, an average of 10.5 per game. If history holds to form, expect to see a Mike White rehiring in 2011.

3. Trading Randy Moss to the Patriots – The Randy Moss era in Oakland will go down as one of the worst marriages in pro sports since Mike Ditka took the plunge with Ricky Williams. By the time the Raiders were ready to move Moss, his value had fallen so far that the Patriots were the only team willing to give up anything higher than a 5th round pick. The Raiders got a fourth round pick and the Pats got a nearly perfect season out of the deal. While the arrogance of the Hoddie was squashed by an epic failure in the Super Bowl loss to the Giants, the Raiders cannot be excused from getting nothing out of the most dangerous weapon in the modern game. Moss has played for the highest scoring offenses in NFL history yet was only good for 6 wins in two years in the East Bay.

2. Brett Favre’s Defining Moment – Brett Favre will be remembered for many things. Among the Favre memories are his myopic attempts to stay in the spotlight and his destruction of the Oakland Raiders only one day after the passing of his father. Favre gave John Madden a Viagra free night on the evening of December 22nd, 2003, by torching the Raiders with 4 first half TD passes in route to a 41-7 spanking on Monday Night. For the rest of the world it was heart warming and inspiring. For Raider Nation, it was sickening and painful.

1. The Painful End to Rich Gannon’s Career – Gannon was the last great offensive player to wear Silver and Black. He was a dedicated leader with a tireless work ethic and a hunger for perfection. The journeymen QB would lead the Raiders to three consecutive AFC West titles, a birth in the Super Bowl and was named the NFL’s most valuable player in 2002. As fate would have it, the Tampa Bay Buccaneers and Jon Gruden were responsible for the decline of the Raider franchise in more ways than one. Gruden’s squad gave Gannon the two worst moments of his career in both the Super Bowl loss and the injury that would end his career. A helmet-to-helmet hit with Derrick Brooks left Gannon with a broken vertebra in his neck. With Gannon’s inevitable retirement, the Raiders have spun out of control and are now mired in the worst six year stretch in NFL history.

Tomorrow, we’ll take a look at the 10 best moments of the last six years. Yes, there are actually 10 of them.

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