Well, unlike some of them at least Jay is getting paid well. Is it worth it? Hard to say. Hopefully Jay is able to take care of his family with the money he has made but it's hard to measure whether the millions he has made is worth the health risks he has taken.
Well, it's like gambling.
If you want to make money, you will have to ruin some of your health. It's not that any guy running a big enterprise, actor or rock star had a healthier life than Jay, with lots of alcohol, junk food, maybe tobacco, other drugs, little sleep, lots of flying and so on.
So eventually Jay will get out of this with some health problems and a good amount of money that he can use to make more money. As you have said, at least Jay is in the position that his gambling will eventually pay off.
What i don't get are the guys that everyone knows will place 10 to last. They ruin they health for nothing.