A password will be e-mailed to you.

No, Oakland Raiders head coach Jon Gruden doesn’t have WR Amari Cooper or DE Khalil Mack anymore, but he does have a 10-year $100 million contract and FIVE (5!!!) first-round selections over the next two NFL Drafts. With the clear mindset of building the Raiders with “his guys”, Gruden is loaded with premium draft capital to hand select his players.

With so many first-round picks at his disposal, it begs the question: What has Jon Gruden done with first-round draft picks in prior drafts? Can Gruden be trusted to cash in and hit on the selections?

Let’s examine every first-round pick drafted under a Gruden-coached team.

Oakland Raiders 1998-2001, 2018

This era probably deserves an asterisks given Al Davis’ control over the Raiders draft room until he passed in 2011. Nonetheless, these are players drafted by a team with Gruden as the head coach.

1998 – DB Charles Woodson (HIT) – Drafting a first-ballot Hall of Famer is the hit of hits.

1998 – OT Mo Collins (HIT) – He was a six-year starter for the Raiders that was selected No. 23 overall. Not a home run but certainly not a miss.

1999 – OT Matt Stinchcomb (MISS) – His career was plagued with injuries, scattering only 20 starts across five seasons for the Raiders.

2000 – K Sebastian Janikowski (MISS) – I don’t care how many kicks he made across how ever many seasons, drafting a kicker in the first round will always be a miss.

2001 – DB Derrick Gibson (MISS) – Gibson was only really a two-year starter and racked up just three career interceptions across six seasons played for Oakland. His contributions were far less than expected of a first-round selection.

2018 – OT Kolton Miller (INCOMPLETE) – We are nowhere near ready to declare Miller and hit or miss.

Three misses and two hits in the Davis-Gruden drafting era.

Tampa Bay Buccaneers 2002-2008

2002 and 2003 – Welp! Gruden was the first-round pick in both years as the compensation Tampa Bay parted with for his services in the trade with Oakland.

2004 – WR Michael Clayton (MISS) – Catching 80 passes for 1,193 yards and 7 TDs as a rookie, Clayton’s career got off to a promising start. He then averaged less than 350 receiving yards per season and scattered 3 TDs over his remaining 5 years with the Bucs.

2005 – RB Cadillac Williams (MISS) – Racking up 1,178 yards and 8 TDs as a rookie, Williams got his career off to a terrific start. The former No. 5 overall pick went on to battle injuries and average less than 500 yards per season with a sub 4.0 yards per carry average. He never lived up to his billing as a top-5 pick.

2006 – OL Davin Joseph (HIT) – A two-time Pro Bowler, Joseph was a seven-year starter after being selected No. 23 overall. He had a solid career.

2007 – DE Gaines Adams (MISS) – Bucs fans still yell at me to this day when I mock them a defensive end from Clemson after Adams was a bust selection at No. 4 overall. He lasted just three seasons in Tampa Bay.

2008 – CB Aqib Talib (HIT) – Gruden’s final first-round pick as head coach of the Bucs was his best one. Talib is a borderline Hall of Famer.

Like his first tenure in Oakland, Gruden finished with two hits and three misses on his top selections. Ironically, Gruden had 5 total first-round picks with both the Raiders and Bucs which is exactly the amount he currently owns over the next two drafts in Oakland. His history drafting beyond the first round is even less inspiring in terms of return on investment.

Would it be considered a success if he again batted 2-for-5? That’s not going to make anyone excited but hitting on these picks will ultimately define Gruden’s second-stint with the franchise. Gruden is betting on himself to draft better than he ever has. He’ll live or die having it his way.