because he's an idiot

when you're born rich you can just keep failing until you don't

*quietly chanting* Lowtax lowtax lowtax lowtax lowtax

That's called loser's bet, or martingale strategy. It's the reason that games like blackjack have maximum bets, so people with enough money can't just bully their way without skill.

"it would be a theme in his life: wasting lots of money and barreling ahead with no strategy"

God hes a dumbass