3. Eric Williams – $40 Million Lost

Eric-Williams

Losing $1 million may be careless, but $40 million? Come on!

4. Scottie Pippen – $120 Million Lost

Scottie-Pippen-e1433671065944

Although a legend on the court, his financial decisions off the court were less than desirable. These included purchasing a $4 million jet that never took off once.