Jay won the sport's highest honor on multiple occasions. One has to assume that he made tens of millions of dollars a year during his tenure. Between contest winnings, endorsements, etc., he must be set for life.
Set for life? I don't see it. He made really good money for a few years but it's all drying up as endorsement deals go to the next new guy. If he didn't invest the money wisely he could have problems. I never knew why bodybuilders and some guys in the NFL with 3 or 4 year careers go off the deep end buying high end houses with a garage full of luxury cars.
Look at how the money can go. You make 4 million in 4 years then your deals all dry up. With that money you think you have unlimited funds. You buy a million dollar house. Close to a half million in cars. Of course you spend 500K on buying a house for your Mom. Your house taxes are through the roof. The taxes on your money is around 40% or higher. With your money you don't open any business that can generate money like a gym or a pizza parlor cause you thought your athletic career would be longer. Now you're no longer in the NFL or Mr. Olympia. Endorsement deals are going to the next new guy. Your income drys of to 35K year in crappy endorsement deals. Your living expenses now put you in negative money.
You would be better off making a million bucks every 9 years like his ex wife does being a top level nurse. I believe she is a nurse practitioner.
I know a guy who was in the NFL for 7 years back in the 70's. He is broke as can be now. Even Lawrence Taylor one of the best players of all time barely can generate over 50k off his name but his name is muddied.