I have never seen such a bad situation, and is going to be fun to try and figure this out.
They currently have 62 players under contract, and according to over the cap, a total of $145 million. According to spotrac, they have a number of 152 Million. The one thing I don't like about over the cap is the top 51 number and the total number, but the top 51 number plus dead money doesn't equal $145 Million, it equals 152 million, so let's use 152 million.
Even worse, is the situation that they are in next year where they only have 39 players under contract, assuming the TV deal doesn't significantly jump like I expect it will.
For the Record, the Romo deal was the dumbest contract I think I have ever seen. With that said, I guess you could convert $12 Million of his salary into signing bonus, and will guarantee he is the quarterback through the 2016 season. That would put him at 37 years old going into the 2017 season. However, even though it will save them $9.5 Million this season, it will give Romo a $28 Million dollar cap number in 2015.
Demarcus Ware has converted part of his salary every season for the last 3 years, and I expect the same will happen this season, since Jerry Jones is an idiot, again assuming that their isn't a significant cap bump in 2015. The smart move is to trade him. If he converts $10 Million to that will save them $7.5 Million as they can only prorate for 4 years. You could add void years for proration purposes, but I didn't.
Brandon Carr converts $6 Million to signing bonuses and saves $4.5 Million
Kyle Orton pay cut to guaranteed 2015 salary of $2.5 Million.
Jason Witten converts $4 Million to signing bonuses and saves $3 Million
Miles Austin June 1st designation cut saves $3 Million
Sean Lee converts $4 Million and saves $3.2 Million
That is a total reduction of $33.2 Million
Extend Dez Bryant with a 5 year contract with a sizeable signing bonus so the salaries are low for 2014 and 2015, and lets use a cap number of $5 Million in 2014.
That puts the 2014 cap number at $124 Million, in addition, they will have to cut 9 players to get down to 53. If they each make $500,000 that would save another $4.5 Million, and if they sign 4 draft picks that is another $2 Million. However they will have about $3 Million in those signings. Net result $3.5 Million savings, and a 2014 cap coming out of training camp of $120.5 Million.
Now, we handled 2014, but as mentioned before, 2015 is a nightmare in itself. They were sitting at about $130 Million, but because of the conversions you have to add $8.3 Million, and you start the process all over again. Plus the Bryant contract minus the Austin cut savings. Pretty close to a wash.
Did I miss anything? I don't enough about the Cowboys to know which high priced players are expendable, and I used the highest players available to just convert. Obviously, straight cuts would be better if possible.