I don't think any of the guys will go broke based on what I watched.
Over the long run (a large sample), poker is a skill. The poker player will always be able to have income coming in because he has developed those abilities. He makes some impulsive purchases...the desire for the island is completely frivolous. Throughout, though, you could tell he understood the money wasn't infinite and his spending had to come back in line to his earnings.
The cash for life lottery winner is smart in that he's getting a degree that will set him up in a secure field. Otherwise, beside investment income he'd count on, he would have no talent to bring in money if it disappeared tomorrow. I think he's more likely to lose it than the poker player. Despite his admirable vision of growing the windfall, you can tell he doesn't have the wisdom or intelligent people surrounding him to make the best decisions. All it takes is a smooth talking person that has gained his trust to put him in a money-losing investment.
I recall the final dinner scene when he says, "a guy" is helping him with the down payment - he's so eager to get started that he's taking a loan on what should be equity on a property - that's a total of 100% loan-to-home value plus fees. Given the risk that the mortgage lender is taking knowing he's using a loan to cover equity, I can guarantee they are not giving him a favorable rate and terms. If either loan is floating rate, there is risk that they rental payments will not cover the mortgage payments in the future. Further, I looked up Franklin Settlements and found barely any information, couldn't find the guy featured on the show, and saw some blogs that were created just to advertise this company - at least he had the intuition to not do the deal with this sleezy salesman, who spent the entire dinner meeting playing on the dreams rather than speaking honestly.
It's clear the average person is too easily swayed by what people say about their goals than the numbers. That's why it's imperative to hire respected advisors after a windfall. I'd even go as far as saying, it's better to spend money on the costlier, but bigger and more established advisory, law, and accountant firms - ones that are globally known/ranked.