The Raiders' Five Worst Offseason Moves of the Past Decade

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The offseason in the NFL is generally a period of renewed optimism, with teams starting over with a clean slate.

For the Raiders of recent vintage, however, the offseason seemingly represents a time of year during which to make regrettable personnel decisions.

With this year’s rather unusual offseason waning, it seems like as good a time as any to revisit, with the benefit of hindsight, the Raiders’ five worst offseason moves of the past decade.

5. Randy Moss (2005)

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Randy Moss, circa 2005 when the Raiders acquired him, was undoubtedly one of the premier offensive threats in the NFL. 

His acquisition inspired hope: the hope that the arrival of the all-world wide receiver, in the prime of his career, would be the catalyst that would lead the Raiders back on track after two disastrous seasons following their Super Bowl XXXVII defeat.

Alas, this was not to be. Moss’ stint in the Bay Area was an unmitigated disaster, with the receiver seeming like a mere shell of his former self for the most part. In fairness, nagging injuries during his two seasons in Oakland limited his ability to earn his keep.

Nevertheless, Raiders brass and fans alike were surely expecting a contribution far greater than his 11 touchdowns and 102 receptions – over two seasons. 

The following season as a Patriot, Randy Moss recorded 23 touchdowns (an NFL record for TD receptions in a season) and 98 receptions. Ouch.

4. DeAngelo Hall (2008)

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When the Raiders acquired DeAngelo Hall in 2008, the sentiment was that the pairing of the Falcons’ Pro Bowl cornerback and All-World Nnamdi Asomugha would prove to be the “second coming” of the legendary Lester Hayes/Mike Haynes duo, the greatest cornerback tandem of all time.  

But it never came to pass. Hall, a zone coverage standout, struggled mightily in the Raiders’ man-to-man system, and was subsequently released at the midway point of that very season.  For his troubles, Hall was paid a cool $8 million by the Raiders for the eight games that he played for them.

He has since regained his Pro Bowl form as a member of the Washington Redskins, having been selected to his third Pro Bowl this past season.

3. Javon Walker (2008)

Dude in the tracksuit? That would be Javon...
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The Raiders rolled the dice when they acquired this free agent wide receiver. Common sense dictated that pursuing Walker, a talented but oft-injured player, at such a steep price (six years for $55 million, $16 million guaranteed) was terribly misguided.

Nevertheless, Al Davis and Co. stuck to their guns and acquired Javon Walker, hoping to prove their detractors wrong. Well, in a nutshell, they proved their detractors right.

In his first season with the Raiders (which, of course, was cut short by injury) Walker only appeared in eight games and recorded 15 catches for an underwhelming total of 196 yards and one touchdown.

In his subsequent season with the team, in 2009, he only appeared in three games and recorded zero stats (in case you were wondering who that dude celebrating in the black tracksuit is...that would be Javon).

The team cut ties with him following that season. All things told, Javon Walker collected $21 million for his “services” to the Raiders. That amounts to $1.4 million per reception.    

2. Aaron Brooks (2006)

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In dire need of stability at the game’s most pivotal position, the Raiders instead cut incumbent Kerry Collins and made the acquisition of the free agent Brooks. 

Brooks had proven to be a serviceable starter during his tenure with the New Orleans Saints but had never really been considered ‘franchise quarterback’ material. Nevertheless, the Raiders handed over the reins of the offense to him.

How did that pan out? Not well. Not well at all. His season was marred by injuries (he only started eight games), inconsistent play (he had a career-low 61.7 QB rating) and ultimately culminated in a 2-14 record, the worst in franchise history since joining the NFL. Brooks was promptly released following the season.

Incidentally, this failed experiment led to the Raiders drafting JaMarcus Russell a couple of months later with the first pick of the 2007 NFL Draft.

1. Jon Gruden (2002)

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Before the arrival of Jon Gruden at the helm in 1998, the Raiders had been mired in a sequence of mediocrity, not having made the playoffs since 1993.

But with an approach that was as steady as it was swashbuckling, Gruden was able to change the collective psyche of his players and, before long, the Silver and Black were enjoying successive AFC West division championships. And then came the offseason of 2002.

Unable to reach a long-term deal with his head coach, Al Davis made the fateful decision of trading the beloved Gruden to the Tampa Bay Buccaneers. In return, the Raiders received the Bucs’ first- and second-round draft picks in 2002 and 2003, and an added $8 million in cash.

The Raiders actually made it to Super Bowl XXXVII that season, boasting a conference-best 11-5 record and the league MVP (QB Rich Gannon).  

But in a cruel twist of fate, their opponents would be...the Tampa Bay Buccaneers. And the rest, as they say, is history.  

The Raiders were no match for their former coach’s new team and the game resulted in a 48-21 smackdown. Coincidentally, this also marked the beginning of Oakland’s downward spiral.