2. Scottie Pippen

-cash blown: $120 million

Scottie earned over one hundred and twenty million dollars during his career with NBA. He then bought a Gulfstream jet in the year 2002. Actually, this is the worst mistake and investment he ever made. It made his bankroll get into a nine million dollar debt to banks and lawyers. The engine of the jet needed one million dollars worth of repairs because a missed inspection.

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The jet got grounded and he sued his attorneys for misinspection, where he got a settlement of 2 million dollars. If only Scottie Pippen had made better investments and didn’t waste his cash on a private jet that he couldn’t even enjoy.