DontMessMe

I think the length was more the issue. The contract was set to run until he was 43 if I recall, even though it was very unlikely he'd play out three entire contract. Because it was heavily front loaded, Luongo wouldn't be giving up much money if he retired before the end of the contract. To make it more obvious, imagine Matthew's signed a 30-year contract and the Leafs loaded almost all the salary in the first 10 years. He could retire with most of that money and the Leafs could spread the cap hit across 30 years, giving an insanely low  cap hit.

It adds 'meaningless' years just to lower the average cap hit. If you really want to sign a guy to a 6 year contract, but sign him to a 12 year contract instead with 6 extra years of 1 million added on to lower the avg cap hit, that's cap circumvention

But, it was cap circumvention that was within the rules. New rules ensure this can't happen anymore. Max contract length of 8 years, max salary variation between the lowest and highest salary years.