The first move has to be resolve the Dak contract. Being specific, I would offer Dak a 6 year deal at $36 million a year and wait for his response. If he is willing to negotiate the term or money, I negotiate with him but I would not give him more than $36 million at year. If he is willing to sign for 6 years, I may be willing to up the average salary a little but under no circumstances will I go over $40 million. If he is unwilling to compromise, I franchise him and try to trade him to a team willing to give him what he wants. But, I will not go into the 2021 season with uncertainty surrounding Dak. In otherwords, I would not keep him on the franchise tag again in 2021.
Next move is to restructure a few deals to free up some cap room. My deal with Dak is going to make some space in 2021 but I want to add to that. I would dangle Amari Cooper out there as trade bait to see what I could get for him. If I can get the right deal for him it frees up a lot of room for defensive free agents. This is unpopular but the trade payoff and the CAP space should ease everyone's concerns.
In free agency, I go hard at the defensive tackles. I like Tomlinson and Rankins. Signing one of them would be my preference. I would also sign Chido Awuzie if he is willing to take a reasonable deal. I am thinking $5 million to $6 million a year is reasonable. Anthony Brown got that last year. If I trade Dak, I'd look for a FA QB but something tells me the best move is the draft.
The draft: If I could not sign Dak, I would look to draft a long term answer at QB. I am not sure yet where the QBs fall in the rankings and I am sure there will be some movement as we get closer to draft week. But QB would be a priority. I would also look for a player like Ryan Fitzpatrick to play until my young QB is ready. Fitz is already practiced at this role.
For the rest of the draft I am focused on defense. CB, S, LB and DT as well as OL and RB for the offense. Best players at these positions in each round. If I traded Dak and Cooper, obviously the extra picks will help restock the WR position.
It is impossible to predict each move because it all revolves around Dak. If he is re-signed then there will be less room for free agents. In that case I focus on DT only. If I get an extra first round pick in 2021 for Dak, I may have to use it to move up for a QB in the first. That changes the draft.
If the Cowboys come out of this offseason without the QB, CB, S and DT positions resolved or upgraded, the offseason will be a failure.