This is probably wrong or has been posted elsewhere... but anyways. What is to stop the following scenario - Say Redden becomes UFA and demands 4.5 million per year - so to sign a 5 year deal, he'll accept 22.5 million. Why doesn't Philly, NY, Toronto, Detroit or one of the other big market teams do the following. Sign Redden to the following deal: Year 1:7.8 million Year 2:7.8 million Year 3:7.8 million Year 4:800k Year 5:800k So the cap hit each year will be 5 million if I understand correctly. NY holds on to Redden for 3 years. They don't care about salary - only about cap hit, so paying 7.8 million doesn't worry them too much since he only costs them 5 million in cap space, which is roughly what he's worth. Then at the end of three years they have this trading chip that is worth a lot. At the end of three years, they trade Redden to some small market team that doesn't care about the cap... only about the actual cost of a player. For instance Edmonton could care less about whether Redden costs 5 million or 800k in cap space, but to get Redden for two years at 800k actual costs would be worth 1st rounders to them. Some real small market teams might even like the extra cap hit, since they can make the salary floor more easily. NY wins because they get Redden for roughly the cap space, and get a fantastic bargaining chip for small market teams at the end of three years. Redden wins because he gets 5 million a year instead of 4.5, and the salary is front loaded so he gets the money quicker. The small market team wins since they add Redden for peanuts in actual costs. Good idea? Huge flaw? Out to lunch? There is a similar potential loophole for small market teams signing players to backloaded contracts and trading them to large market teams.