you know, i've seen situations where two friends live seemingly similar lifestyles while one was earning over double what the other earned.
after a decade or two, the higher paid one goes bankrupt, while the one with the lower income ends up with his house paid for. what you see someone publicly spend isn't always the whole picture. high paid people often spend every sent, and then some; thinking they will always have that cashflow. others know the income may stop and prepare for the long haul.
don't know cutler's case, but he may have a poor man's mentality, and despite the flash, did the right things with a percentage of his wealth and set himself up. or, like thousands of pro athletes have proven, it's easy to blow through millions if you don't have a clue.