Restructuring contracts does cost more money. If you realize after 3 years that a 5 year $100 million contract is a mistake you might get out of it after paying $60 million over 3 years. But if you restructured it every year and had to face a $40 million dead cap hit if you moved on under year 3, you may be forced to restructure the contract for year 4 to delay the $20 million due, then face even larger dead cap leading into year 5 leading to another restructure. When the contact is set to end after Year 5, you may face a $50 million dead cap hit, and instead choose to pay a backup $15 million, a 'generous pay cut' of much more than his market value. So in the end you don't pay the same you pay $115 million instead of $60 million, and as a reward you potentially block upward mobility for your players, hold roster spots for veterans you are only keeping for financial reasons, and send the message to all your stars that their jobs are safe even if their production drops and to all your younger players that there is no room for them to start because some 30-somethings contract is too big to fail.

Dead cap is much higher, and the spare salary cap space to absorb dead cap hits is much lower, under Mickey Loomis's accounting.