I do know that the Cowboys have less than $1 mil in dead money. Also they could clear as much as $80 mil if the really wanted to. I doubt they clear that much space though. No sense in reworking Romo's contract.
Dead money isn't the problem for Dallas. The problem is the team has a disproportionate amount of cap dollars tied up in the form of previously prorated base salaries.
They have a cap total of $146.1M right now (team cap of $158.8M) and only $105.2M in cash spending. That's $41M in cap space that is attributed to prorated bonus money and dead money. They only have $900K in dead money so $40M of their salary cap is comprised solely of cap charges that are a result of prorated money. That would be 2nd highest total in the NFL with only Baltimore having more. The Ravens have $500K more than Dallas.
The league average is $17M. Well above average and the number is a bit shocking considering that we are now 2 (maybe 3 seasons) into the new and improved Jerry Jones cap management era.
They have to sign both Osweiler AND Von. Von will get franchised. I'm betting there will be a fight between Von Miller and team because Von will want to get paid like a DE and not an OLB. Same thing that happened with Suggs and the Ravens a couple years ago. Then the Broncos will have to outbid teams for Osweiler. They could easily use up their entire cap on those two players alone. I still think Ware would agree to a paycut to stay there though.
Only if they structure Osweiler's contract to do so. They could overpay him by a mile, take a small cap charge this year and then take large cap charges starting next year when they have free space currently projected at $86M
They could hand each of those guys 5 year, $80M deals. Take $8M in cap hits in year 1 and $18M in cap charges for the remainder of the contract for each guy. That'd leave them with $11M this year and $50M next year.