Good thing he has a new house. That old one was way too small for 2 people and a few dogs. 
Nice things are great and if you can afford them and they make you happy, more power to you. You have to wonder though how long he'll have to enjoy his new place and cars. All that substance abuse adds up, believe me. These guys live in the land of make believe where they look good, so they must be healthy.
I'd place more importance on my family then winning another few titles which in the long run, don't come close to the people you love. Who knows though, he could live until 70 
i played baseball a few years in the minors. ended up getting released. i went to college before that, but didnt care much for my major -which was special education (because thats what i could fit in).. i spent a year not knowing what to do with my life, up to that point baseball was all i ever wanted to do, and its all i was good at..but i remembered i really liked a criminal justice class i took.. ended up getting into the nypd.
its an extremely dangerous job when your chasing drug dealers and breaking down crack houses in the south bronx.. been shot at several times, beaten, stabbed, you name it... every time i strap on that vest i know it could be the last time.. but its what im good at, and its all i know, and its the best way for me to provide for my family(just a wife so far). luckily i got promoted to a different department. bought a house, nice car, new boat. im not sure how long ill be able to enjoy those things either.
i can imagine jay's in the same boat im in. if i was ever killed, i know my family would be taken care of because of what ive done,,and thats more important then how long i live,, same as jay. when you see that money comming in and the stability its giving you, how can you turn it down and risk doing something else? maybee jay has insurance and assets that will take care of them when hes gone. when you factor that stuff in you can realize why some people put their own health and safety at risk.