We basically structure the deals to fin inside the parameters the rest of the league uses. Then we look at the deals that are performing well and convert them as we need cap space, eating the underperforming deals as we go. If we're snug against the cap, it's because we've been fairly careful about not converting some deals that don't look good for us right now.
Our biggest hits in recent years have been the Carr/Witten/Dez/Romo deals. You can't blame the Cowboys for having a big number on their franchise QB in his 30's. Other than that, though, they have been leaving the Carr and Dez deals alone. Our dead money numbers aren't bad these days. Basically, we're signing our own, absorbing the deals that look less promising, restructuring the ones that look promising as we go in order to free up space to sign more of our own players. We'll get a bump when Romo's off the roster for a year or two until we have to extend Dak. This means there have been a couple expensive deals we've had to absorb, along with having a huge piece of our cap on the sideline the last two years due to injury/Dak's performance. Other than that, though, we've been pretty responsible.
The only real beef I've got with our cap allocation is that we spend $2 on offense for every $1 of defense and expect to be able to stop Aron Rodgers that way.