Year: 2008
Net worth: $270 Million

Back in 2008, when LeBron was enjoying his first stint in Cleveland, the King decided to pop into XO Prime Steaks with his entourage for a little late-night meal. And by late night, we mean he was reportedly there until about a quarter to four in the morning. And by little, we mean the bill came to $800. Now, we’re not trying to say that just because LeBron has money he should throw ridiculous amounts of change at people. But leaving the alleged $10 tip that he did on this meal is a little bit appalling.

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