Year: 2005
Net worth: $50 Million

When you earn the nickname “No Tippin' Pippen,” you know your reputation as a scrooge probably isn’t something that’s just being imagined by a few angry folks in the service industry. Apparently, Scottie Pippen’s cheapness had no limits. He even went as far as to attempt to negotiate some strippers down from their regular fee at the Penthouse Executive Club once. Come on, Scottie. If you’re trying to negotiate strippers down from their normal fee, you’re probably in the wrong place to begin with.