I'm not sure exactly what you're asking, but yes it is standard procedure to backload deals, but there is a limit. When you cut somebody, all the cap money accelerates onto one year (unless after June 1st, in which it's split in half for the next two years). Let's say the Bears converted Cutler's salary for the next 3 years into signing bonuses. It works out that with the different prorations that his cap hits for each of the first three years would be around 4 million apiece. If they kept Cutler for year 4 in that scenario, his cap hit would be 21.5 million (with the years after that being even higher than that). If they cut him, his cap hit would be 35.9 million in dead money! If Cutler starts to struggle (say he puts up a season similar to Eli this year in year 3) the Bears would have a tough decision. They couldn't afford to cut him and take all that dead money, but they don't really want to keep paying him 20+ million to keep him either. That's the other danger in backloading besides of course just running out of money by backloading too many players. Of course hopefully Cutler doesn't struggle like that, but the Bears seemed to want to protect themselves long-term which is why they structured the deal the way they did. They have minimized the risk by giving him so many team options at the end of his deal, and if they end up converting some of it into signing bonus that will still mostly be the case. I think they gave themselves both options. They can hopefully keep this unique contract, but if they convert a modest amount into a signing bonus it will end up looking more like a regular contract. Some teams have taken this approach of loading up for a few years and then just blow up the team, but it's not usually the way teams like to operate. When the Colts for example lost Manning, they cut a bunch of other veterans and took 40 million of dead money in one year. The Raiders did the same thing this year and have even more dead money. I wouldn't necessarily assume the cap will keep increasing, at least not very much. After this year, it will have only gone up 3 million in the last 5 years. Most of the explosion in money has already happened for the NFL, and I think most expect only small increases in the cap in the years ahead. That might have confused rather than helped, so feel free to ask more!