2019 NFL Draft: How should the Raiders approach each stage? Let's play GM and take a look

With the exception of the Arizona Cardinals, who own the No. 1 overall pick, no NFL team is in a position to dictate the course of the 2019 draft more than the Oakland Raiders. (The Cardinals also rank first in draft capital, while the Raiders rank second.) Jon Gruden, Mike Mayock and company own four of the first 35 picks in the draft, including three in the first round. Oakland still has more than $32 million in cap space available as well, which means the Raiders can go in pretty much any direction they want when next Thursday rolls around, including trading picks for players.

Below, we'll walk through all the different options the Raiders have at each stage of the draft, and how best to approach them. 

Round 1

Picks: No. 4, 24, 27

The way I see it, there are four main options here. Let's tackle them in order of how drastically they would affect the Raiders' strategy for the rest of the draft.

  • Trade up for the No. 1 overall pick.

There is really only one reason to trade up to No. 1: Kyler Murray. There are enough high-level defensive prospects that staying at No. 4 and taking whichever one falls into your lap would be just fine. By contrast, if you want the top quarterback in the draft, you almost always have to jump to the No. 1 pick in order to get him. 

As for the actual draft, you'll be able to stream our live coverage right here on CBS Sports HQ (or download the CBS Sports app for free on any mobile or connected TV device) breaking down all the picks and everything you need to know during draft weekend. But before that, you should join us for our live mock draft show on CBS Sports HQ from 4-6 p.m. ET today -- yes, today! -- where all your favorite NFL personalities will run through the first round playing general manager, with trades, analysis and plenty more. You can find that from 4-6 p.m. ET at this link.  

Rumors have obviously been swirling for weeks that the Cardinals want to grab Murray themselves with the No. 1 pick if they can find a taker for Josh Rosen; but if the Raiders feel strongly enough that Murray is the answer at quarterback, then they have to put in a call to Steve Keim regardless of what they think the Cardinals' plans are, and find out what it would take to get the No. 1 pick off their hands. Something like No. 4, 24 and 35 for No. 1 and 65 would seemingly be an agreeable deal. On the Jimmy Johnson draft value chart, the Raiders would sent out 3,090 points and receive 3,265 points, but on the more analytically-inclined Chase Stuart chart at Football Perspective, the Raiders would send out 52.2 points and receive 42.6 points in return. 

Making a move like this would require changing almost the entire plan for the rest of the draft. Not only would the Raiders be down to two first-round picks instead of three, they'd also lose their pick at the top of the second round. And by bringing Murray into the fold, they would be signaling that they're no longer interested in keeping Derek Carr, who would become an immediate trade candidate but whose value would be presumably be lowered because everyone would know the Raiders were no longer committed to him.

If the Raiders do not feel Murray is worth trading up for, that opens up several different paths.

  • Pick at No. 4 and package No. 24 and 27 to move back into the top half of the first round.

Even in this scenario, there are two different paths depending on what Arizona does at No. 1 and whether another team elects to trade up for Murray. If the Cardinals take him, then one of the elite defensive prospects in the draft is going to be there at No. 4, and the Raiders just have to decide which of the remaining players they like best. If the Cardinals trade the pick to someone else who grabs Murray at No. 1, then the plan remains the same, just as it does if the Cardinals pick someone else and then a team trades up to No. 2 or No. 3 to draft Murray. 

In a scenario like that, at least three of the following players will be on the board at No. 4: Nick Bosa, Josh Allen, Quinnen Williams, Ed Oliver, Devin White, Montez Sweat. Bosa appears to be the only stone-cold lock to go in the top three picks, which means any of the other five players could conceivably be available. The Raiders have needs all over their defense and don't necessarily need to be pigeonholed into taking an edge rusher or an interior lineman or a linebacker; they can just take whichever guy they like the best. 

If they want to go the route of drafting at No. 4 and then moving back up, ideal teams to target would be the Bills at No. 9 and the Dolphins at No. 13. If they can get into one of those spots, with one of the six aforementioned players still on the board (or even someone like Devin Bush or Brian Burns, if the Raiders think that highly of him), that would allow the Raiders to double-up on elite defensive prospects and add a ton of talent in one fell swoop. Could Oakland come out of the draft with Allen and Oliver? Williams and Sweat? White and Burns? Any of the linemen and Bush? All are intriguing possibilities. 

Things get even more interesting if the Cardinals, 49ers and Jets all pass on Murray and he's still available at No. 4. What do the Raiders do then? Gruden is reportedly very high on Murray, and it would be difficult to see the Raiders letting him slide past -- even with Carr already on the roster. In such a scenario, would they still trade up to nab a top-level defender, or would they need to hang onto their picks in order to fill out the roster around him?

  • Trade down from No. 4 for even more picks.

This is where we acknowledge that while the Raiders do have three picks in the first round and four of the top 35, and that they did trade for Antonio Brown and sign Tyrell Williams and Trent Brown and Lamarcus Joyner, they still have an extremely thin roster with a whole bunch of holes and also do not have many mid-round picks. (More on that below.) 

If they decide that the best course is to trade down and pick up even more value, the best case scenario is Murray falling out of the top three and enticing someone else to offer the Raiders more than they can refuse to move down. Even if he doesn't, though, it's possible someone could want to move up for their choice of the aforementioned defenders, or even Dwayne Haskins. The Raiders have so many holes on defense that it might not necessarily matter which one of those guys they get, but they should be careful not to move too far down the board because they do still absolutely need to add high-level defensive talent. (The Bengals at No. 11 are the lowest I'd be willing to drop, and the price would be pretty high for doing so.) 

  • Stay put and make all three picks.

Of course, there is always the option of just sticking at No. 4, 24 and 27 and picking the three players the Raiders feel are the best at those spots. This would allow them to add add one of those elite defenders, plus fill in another spot on the defense and grab a skill-position player or offense. Or they could just load up with three defenders. It's all about options. 

The way the draft unfolds obviously plays a large role in which of those options is ultimately pursued; but if I'm the Raiders and I keep all three picks and make a selection at those spots (none of which is Murray), I want to make sure I have filled three of the following positions: edge, interior defensive line, defensive back and wide receiver/tight end. 

That means looking at guys like Dexter Lawrence, Jerry Tillery, Christian Wilkins, Jeffery Simmons, Rashan Gary, Clelin Ferrell, Chase Winovich, Byron Murphy, DeAndre Baker, Greedy Williams, Jonathan Abram, Chauncey Gardner-Johnson, Juan Thornhill, Taylor Rapp, Nasir Adderley, Marquise Brown, A.J. Brown, D.K. Metcalf, N'Keal Harry, Hakeem Butler, T.J. Hockenson and Noah Fant.

Day 2

Picks: No. 35

Unless a player on whom the Raiders have a first-round grade drops to them, I consider this an ideal spot for the Raiders to trade back. As previously mentioned, the Raiders do still have a whole lot of holes on their roster, and they do not have a single pick between No. 35 and No. 106. If they can entice a team into offering their third-round pick to move up from the middle of the second to No. 35, that would be excellent. If Washington or Cincinnati wants to move up and grab a sliding quarterback, or the Ravens want to jump up ahead of the wide receiver run, for example, they would all make for interesting partners. 

If none of that materializes, they should be looking at the group of players mentioned above once again, allowing how the draft has unfolded to dictate in which direction they ultimately go. The following player groupings all seem both within the realm of possibility and beneficial for the Raiders (and keep in mind these groupings could easily be mixed and matched in other ways, and that someone like Bush or Burns could even drop to 24 and be available to throw in the mix):

  • Josh Allen, Jerry Tillery, DeAndre Baker, A.J. Brown
  • Quinnen Williams, Byron Murphy, Clelin Ferrell, Noah Fant
  • Devin White, Christian Wilkins, Jonathan Abram, N'Keal Harry
  • Ed Oliver, Rashan Gary, Chauncey Gardner-Johnson, Hakeem Butler
  • Montez Sweat, Dexter Lawrence, Marquise Brown, Juan Thornhill
  • Kyler Murray, Greedy Williams, Marquise Brown, Jeffery Simmons

Any one of those scenarios would allow the Raiders to add high-level talent at multiple positions while also filling areas of major need. That's the kind of position you're in when you own four of the first 35 selections in the draft.

Day 3

Picks: No. 106, 140, 218, 235

Pick No. 106 seems like a prime area for the Raiders to add a running back. Using one of the top four picks on one when they have so many other needs seems unwise, but so does entering the season with Isaiah Crowell, Jalen Richard and DeAndre Washington leading the backfield. The fourth round could see players like David Montgomery, Justice Hill, Damien Harris, Miles Sanders or Darrell Henderson available, and the Raiders would do well to add one of those talented players to the running back room. 

If they don't take a quarterback early, adding someone like Will Grier, Jarrett Stidham or Ryan Finley in the mid-rounds as a developmental prospect could be a nice pickup as well. Adding talent along the offensive line -- especially if they draft Murray early on -- and at linebacker should also be in consideration, as should whichever of the positions mentioned above (edge, interior defensive line, defensive back, wide receiver/tight end) still need filling out after the early picks are made. Because the Raiders will be so busy early on, they can largely sit back and let the rest of the draft come to them, picking and filling needs as they see fit. 

CBS Sports Writer

Jared Dubin is a New York lawyer and writer. He joined CBSSports.com in 2014 and has since spent far too much of his time watching film and working in spreadsheets. Full Bio

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