Year: 2002
Net worth: $1 Billion

Apparently, the G.O.A.T. on the basketball court was not the G.O.A.T. when it came to taking care of those in the hospitality industry. From Chicago to Washington, D.C., Jordan’s reputation as a miser is somewhat legendary. It’s said that MJ would routinely run up bills of $1,000 or more in Chi-town and not leave a single dime for the wait staff. Once described by Charles Barkley as being “as cheap as they come,” Jordan’s lack of generosity followed him in the later stages of his career in D.C. as well. The greatest story, though, has to be when he and Wayne Gretzky were sitting at the tables in Vegas, and the Great One called out Jordan for tipping a waitress $5 for a drink. Apparently, Gretzky took back the five, gave her a hundred, and showed MJ how it’s done in the desert.

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