Here is how you waste that million bucks in a year or two
buying 2 Bentleys 
The average american makes what 55k or so a year? I'd say the average cost of a new vehicle is 25k, or roughly 50% of the average American's yearly income. Last year "situation" made 5 million. Those two vehicles cost about 500 grand total, or 10% of his yearly income. That's not even getting into the fact that they hold their retail value and are collectors items. So, no, that's not why he'd go broke.
Even if situations income decreased 25% per year over the next three years ( which it wont - it will increase, and then drop off a cliff) he can more than afford those cars. Anyone who's made 5 millions bucks from a trashy tv show is not an idiot.
In a nutshell, it's like you making 100k per year, and driving around in a vehicle that cost you 10k... a vehicle that you can resell for 7k in a few years.