Michael Jordan is still the wealthiest athlete in the world, even though he retired from the NBA almost 20 years ago. With an estimated net worth of around $1.6 Billion, it's evident Jordan made the right business moves throughout his career and expanded on that after he retired. People with that much money spend it in various ways, with some being more diligent with their financials and some looking to spend it in all sorts of crazy ways.
According to Rich Strafella, former VP of Hard Rock Hotel in Las Vegas, Michael Jordan is considered cheap and shared a story of Jordan gambling with the legendary hockey player Wayne Gretzky. Apparently, Jordan didn't know the ropes of appropriately tipping in Las Vegas, and it came out as he was cheap in front of others. Strafella remembers Jordan ordered a drink and only gave $5 to the waitress, which immediately triggered Gretzky, who had to step in and show how things are done in Las Vegas.
I remember a night when Wayne Gretzky insulted Michael Jordan at the table. It was a private salon game. Michael had ordered a drink from the cocktail waitress, and he gave her a five-dollar chip. Wayne took it off the cocktail waitress's tray, gave it back to Michael, grabbed a hundred-dollar chip from Michael's stack, and put it on the cocktail waitress's tray. Then he said, "That's how we tip in Las Vegas, Michael.
Rich Strafella, via The Sports Rush
Gretzky was obviously more experienced about tipping in Las Vegas than Jordan was at the time, and rarely someone would have the nerve to casually take Jordan's chips and give them as a tip. That just showcases what type of alpha mentality Gretzky possessed even when Jordan was on the other side of the room.
However, Charles Barkley was another person that pointed out Jordan was cheap on several occasions, often calling out Jordan for being so strict with his money. One time they even talked about it while making an appearance on The Oprah Show. Barkley wanted to give a homeless man some money, and it was Jordan that stopped him and said the man could easily find a job in McDonald's instead of asking for money on the streets.
“I was gonna give a homeless guy some money one night, and he slaps my hand. And he says ‘Well if he can say do you have any spare change, he can say Welcome to McDonald’s, how can I help you?'”
Charles Barkley, via The Oprah Show
These types of stories showcase Jordan's personality or at least one part of it related to money. For him, it was always about hard work and not being given handouts, so that translates into how he operates with other people, in this specific case with the waitress that brought him his drinks. Whether you want to describe his actions as cheap or not, it doesn't matter because Gretzky was there to save the day and give the waitress a Las Vegas-worthy tip.