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Well, if most players are broke shortly after leaving the league, then that's their own fault for taking the league minimum contracts! Football players are worth more than what they're getting in contracts, but teams try to coerce players to take the minimum deal simply because "bUt ThE cAp!". Last time I checked, the cap wasn't a player's problem, it was team management's.
What DiNozzo is doing is saving up his money from his playing days, and investing them into various companies that are developing some promising technology. Did you know that this company, Tesla, is making a self-driving car? How convenient is that?! There's also GameStop, which is a meme stock that DiNozzo likes simply because he's a video game nut. It's gotta be worth more than $4 a share at some point, right?
There's also this opportunity to fund a professional wrestling promotion called All Elite Wrestling with Tony Khan. Word has it that they have a talented roster ready to go, but needed just a little bit more money in order to secure a television deal. If that takes off like DiNozzo thinks it will, it'll print money, bay bay!
So, while DiNozzo is doing these outlandish things, he's being smart about where he's investing his money. How will DiNozzo do after he retires? Who knows. If he's not successful and broke, he'll blame league management for coercing him into taking the minimum value contract, as he should.