@Spurt
The Cowboys aren't in the worst situation of any NFL team in terms of the cap, but they've got issues. The Cowboys and Bills are in a similar spot. Both expect to contend, but neither one can afford their current roster, let alone add to the roster, and both need help at multiple positions. The Bills have opted to cut a lot of players to create cap space and hope they can fill in with whatever they add in the draft.
With both teams drafting in the latter half of the first round, it's trickier finding "sure thing" starters. You're largely hoping for the best.
The Cowboys may have camp issues also if they don't extend their guys early. If they don't have extensions with guarantees in place for Dak, CeeDee, and Micah, would any of them report to camp and take the risk of getting injured? They won't want to go out in practice and tear an Achilles or ACL. The agents for all three guys should hold them out of OTAs and camp until they have a deal in place.
JJ's apparent desire to wait until August to work out a deal for Dak means he expects Dak to show up for camp and put in a week or two's work before getting a new deal. I wouldn't do that if I were Dak.
You don't want to be Mike McCarthy and have Dak, CeeDee, and Parsons all sitting out camp due to contract issues that could have been, should have been solved earlier. You'd prefer to solve contract issues before they become issues.
I'm not sure I wouldn't try a Herschel Walker type of deal using Micah Parsons as Herschel Walker. Would Washington part with that second overall pick and more for Parsons? Maybe. Would the Bears give up pick nine and a boatload more picks for Parsons? At nine, JJ could draft one of the best edge rushers in the draft to replace Parsons at a much lower cost and save about $35 million in cap space going forward.
If JJ pays Dak, CeeDee, and Parsons, top of the league money ($60 million for Dak, $30 million for CeeDee, and $40 million for Parsons) that's $130 million or about half the current $255 million cap. On three players. You then have to divide the other half of the cap among fifty players. It's not an especially sustainable way to run an organization.
You can't trade Dak due to the stupid contract you gave him, so you're stuck with him. At least for this year. CeeDee is not the hottest tradeable commodity. You could get a mid-first-round pick for him, but you'd then need to use that pick to replace him. And of the big three, most expensive guys, that leaves Parsons. Dan Quinn knows him well and would drool at the prospect of him being a Commander. And God knows the Commanders could use an edge rusher since they traded their guys away last year.
That second-overall pick would have significant value for Dallas. They could hold it and draft Dak's lower-cost replacement for next year. They could trade down and pick up more draft picks, and maybe a player or two from a team desperate for a QB. It would give them lots of options and solve some of their problems. At least in terms of the salary cap.
It's hard to see a way the Cowboys can sustain success if they pay all three guys at their fair market value. Having the league's highest-paid guys at three positions is a salary cap nightmare. Something has to give. The players won't take less than they're worth, so you either have to pay them or move on. Parsons is a highly valuable guy as a trade asset. Put him on the market and watch the offers roll in. You save about $40 million in cap space and gain a bunch of cheaper, younger players.
Fly!!! Eagles!!! Fly!!!