Say what you want about the start to Jon Gruden’s second tenure with the Raiders, but the polarizing coach-turned-commentator-turned-coach-again has done an amazing job acquiring early draft picks from other teams. 

Somehow, Gruden got a first-round pick from the Cowboys for Amari Cooper, a super-talented but super-inconsistent 24-year-old with a $13.9 million cap hit next season. 

And for as fun as free agency can be, we all know championship caliber clubs are built through the draft. 

If this is possible, for a few minutes totally ignore the players Gruden has sent packing so we can dive into the embarrassment of riches the Raiders head coach now has on the draft front and identify potential prospects he could select with the team’s three first-round picks in 2019. 

(Before I begin: While I absolutely would’ve paid Khalil Mack anywhere between $20M-$25m per season, the idea for Gruden to look at his 2018 roster, start somewhat of a fire sale to gain valuable draft capital and sign older, cheaper players to one-year contracts to free cap space in the future isn’t crazy and just might ultimately work.)

Pick No. 1-5 Overall  

Right now, the 1-5 Raiders are projected by SportsLine to win the third-fewest amount of games in the NFL this season (four). The 1-6 Cardinals (3.7 wins) and 1-6 49ers (3.8) are the two teams currently with lower projected win totals. 

Unless the Raiders go on a unbelievable second-half-of-the-season run, it’s safe to assume they’ll be picking somewhere in the top 5 of the 2019 Draft. 

What Raiders should look for

With Khalil Mack now wreaking havoc for the Bears, the Raiders need an alpha pass-rusher on the outside. Even the casual NFL fan knows that. Picking the top 5 means you have a lot of work to do personnel-wise and you need to pick a high-caliber player at a premium position. While defensive tackle isn’t a classic, high-value position, with the way the NFL is centered around the quick-passing game, the defenders closer to the ball are becoming more vital to defenses every year. 

(With Jason La Canfora’s sources telling him of Justin Herbert “it is far more likely that the junior actually remains in school for another year,” along with my hunch that Oakland will hang onto Derek Carr, I’m leaving quarterback off the radar for the Raiders for now.)

Pick Candidates

Nick Bosa, DE, Ohio State – This is the slam-dunk no-brainer for the Raiders. He’s the most NFL-ready pass-rusher since … his brother in 2016 and has All-Pro potential. He’d instantly slot into the gigantic hole left by Mack’s departure and boost Oakland’s league-worst pass-rushing unit. His core injury should be fully healed by the pre-draft process. 

Ed Oliver, DT, Houston – Oliver has a decent chance to be a Raider in 2019. Hear me out on this. While roaming the sidelines in Tampa Bay, Gruden coached Warren Sapp, an “undersized,” lightning quick defensive tackle who’d eventually make the Hall of Fame. I won’t call Oliver the next Sapp, but he’s the most athletically impressive defensive tackle to enter the NFL since Aaron Donald in 2014, a player on track to, like Sapp, make the Hall of Fame as a one-gapping backfield disruptor. Yes, the Raiders drafted pass-rushing defensive tackle Maurice Hurst and P.J. Hall in 2018, but if Bosa’s gone when the Raiders go on the clock, I think Oliver should and will be in play.

Clelin Ferrell, DE, Clemson – If Bosa and Oliver are off the board when the Raiders make their first pick in the 2019 Draft, Ferrell would certainly be a viable option. The long, well-built defensive end has steadily improved during his Clemson career and has started to flash pass-rushing moves more often to go along with a solid speed-to-power bull-rush and bend around the corner. To date, Ferrell has 41 tackles for loss and 21.5 sacks since the start of 2016. 

Pick No. 13-19 Overall

After their three-point loss to the Redskins in Week 7, the Cowboys are slated to finish the season with eight wins, which right now equates to the No. 15 overall pick. Because eight wins wouldn’t get Dallas into the playoffs, the latest their pick — which is now the Raiders selection — could be is No. 19 overall. 

What the Raiders should look for 

There’s more leeway in regards to positional value as you move into the middle portions of the first round. The Raiders have a myriad of holes on the defensive side of the football that will disallow them from staying competitive even if they build a dynamic offense again. Two of the four cornerbacks who’ve currently played the most snaps for the Raiders thus far — Leon Hall and Dominique Rodgers-Cromartie — are already in their 30s. Rashaan Melvin will be 30 next October. That’s a need. So is safety with 2017 second-round pick Obi Melifonwu already waived and 2016 first-rounder Karl Joseph closer to being a bust than a player worthy of a contract extension. Game-changing safeties aren’t easy to find, but the teams that have them typically thrive stopping the pass. 

Now that Cooper’s gone, Jordy Nelson and Seth Roberts are the only Raider receivers under contract for 2019. Carr — or whoever’s playing quarterback for the Raiders in 2019 — needs a larger arsenal of wideouts, and that position is now highly valuable in today’s NFL, seemingly a necessity to field a championship-level team.

Pick Candidates

Devin White, LB, LSU – It’s not as obvious as defensive end, but Oakland has a glaring need at off-ball linebacker. And again mentioning Gruden’s past, he did coach Hall of Famer Derrick Brooks, one of most athletic linebackers in NFL history. Like with the Oliver-Sapp comparison, I’m not labeling White as the next coming of Brooks, but there are similarities between the two. White’s a twitchy, ultra-aggressive linebacker who, as a 20 year old, probably has his best football in front of him. He’s a little slow reacting to his keys and is a liability as a tackler but plays with his hair on fire. I think Gruden would love what White brings to the field. 

Brian Burns, DE, Florida State – If the Raiders aren’t able to snag on an outside-rusher with their first of three Round 1 selections in 2019, Burns would be one heck of a consolation prize here. According to Pro Football Focus, the angular Florida State defender leads the nation with 46 quarterback pressures, and, like White, is theoretically a high upside prospect at just 20 years old. He routinely wins with a scary combination of burst, dip, and bend to the quarterback and has tentacles for arms. With more weight and power, he can be a dominant defensive end in the NFL. 

Deionte Thompson, S, Alabama – This is partially a byproduct of the lack of pass-rush, but the Raiders only have four interceptions in six games, and 35-year-old safety Reggie Nelson has one of those picks. Thompson is the top safety prospect in this class and very versatile. Despite his lanky frame, he delivers big hits on running backs often and has awesome range from center field.

Amani Oruwariye, CB, Penn State – After Greedy Williams and Deandre Baker, Oruwariye will be in a fight with few others to be the third cornerback taken in the 2019 Draft. Blessed with explosiveness and fluid athleticism, the 6-foot-2 Penn State corner glides across the field and has the length and athletic talent to make plays on the football with impressive regularity. 

N’Keal Harry, WR, Arizona State – Harry has been a productive receiver since his true freshman season at Arizona State and though he’s mostly known for his size and awesome contested-catch ability, he has open-field wiggle and deceptive long speed. Per PFF, Harry has forced the 13th-most missed tackles after the catch in the nation at 6-foot-4 and 213 pounds. 

Pick No. 19-24 Overall

The Bears‘ win-total project by SportsLine currently sits at 8.5, which would give the Raiders the No. 19 overall pick in the 2019 Draft. If Chicago outperforms its projection, the Bears could make the playoffs, meaning they’d be guaranteed to own the pick now going to the Raiders somewhere in the No. 20 overall – No. 24 overall range.

What the Raiders should look for

While the Raiders defense needs an overhaul — Oakland’s allowing the most yards per play (6.7) in the NFL heading into Week 8 — the offense needs an influx of talent too. The Raiders are averaging 5.7 yards per play on offense, the 17th-highest figure in football. 

Kelechi Osemele was once an elite guard, and Oakland paid him like one with a five-year, $58.5 million deal in 2016. However, like most NFL contracts, it had an easy out after two seasons. He’s battled injuries this season and his play has trended in the wrong direction after a stellar debut campaign with the Raiders. If he’s cut in 2019, Oakland doesn’t carry any dead cap. As the value of defensive tackles increases, so does the value of offensive guards. 

Pick Candidates

A.J. Brown, WR, Ole Miss – While there’s a good chance Brown is gone by this pick, as a pass-catcher who predominately works out of the slot and probably won’t run incredibly fast at the combine, a fall into the latter portion of the teens wouldn’t be shocking. Brown is a muscular, yards-after-the-catch monster with strong hands and high-point ability. 

Dre’Mont Jones, DT, Ohio State – Though not as explosive up the field as Oliver, Jones is much further ahead with his pass-rushing moves, and he’s certainly not a stiff athlete in his own right. He’d formulate a tremendous inside pairing with Hurst for the Raiders. 

Taylor Rapp, S, Washington – Like Thompson, Rapp is a do-everything safety who seemingly moves at a different pace than everyone when he’s on the football field. His production has been down since a four-interception freshman season in 2016, but Rapp’s can play the nickel ‘backer role in today’s NFL then slide back to deep safety on the next play. 

Jachai Polite, DE, Florida – Polite needs to add more power to his game, but he has the most dazzling flashes of any pass-rusher in this class not named Bosa or Burns. Polite is a pure speed/bend-rusher, has a spin move in his arsenal and, on occasion, uses his hands to defeat offensive tackles at the point of attack. 

Michael Jackson, CB, Miami – Jackson’s an overwhelming physical presence at corner at 6-2 and close to 200 pounds. He had four pass breakups and four picks last year and has already defended four passes in 2018. He has the size, length, and strength to handle big, outside receivers in the NFL. 

Ben Burr-Kirven, LB, Washington – A draft riser, Burr-Kirven was made for the modern NFL. He’s half safety, half linebacker and is always around the football. He already has 108 total tackles, one pick, and three pass breakups for Washington in eight games this season. If Gruden wants speed and coverage ability in his linebacker room, Burr-Kirvin will definitely be on his radar. 

Josh Allen, EDGE, Kentucky – It’s hard to peg where Allen will be selected in the 2019 Draft. Per PFF, he has 36 quarterback pressures on just 161 pass-rushing snaps thus far in 2018 from his stand-up linebacker spot. That pressure rate of 22.3 percent is a really good. However, Allen’s a player who almost solely relies on his physical ability to beat offensive tackles. His speed around the edge is excellent though. If he shows more of a willingness to use his hands while rushing the passer and develops some counter moves, he’ll be a more highly-sought after prospect and a better pro. If the Raiders don’t address edge-rusher with their first two picks, the Kentucky star would be logical here.