If you ever have the ability and opportunity to invest in a professional sports franchise, you do it. They are quite possibly the sole investment that actually only goes up.
Now, sure, on the surface this looks bad for John Elway. All-time bag fumble. But in 1998, Elway had made $45 million in on-field earnings. Let's be generous and say he matched that in endorsements, giving him a total of $90 million — and obviously he had spent some of that in the 15 years he'd been playing. So $38 million was no small investment.
Obviously he wishes he had done it now that the team just sold for $4.5 billion, as anyone would. But maybe he made other investments with that money that turned out to have really good returns. Probably not 2,500% good, but good nonetheless. And I'm sure Elway is doing just fine, but the difference in being a hundred-millionaire and a billionaire is enough to keep you up at night — at least I'd imagine so.
Again, if anyone ever approaches you with a chance to buy any percentage of an NFL, NBA, MLB or NHL franchise, you find a way to get it done.