More stories I found online after being inspired by this thread:
Bill Clinton
They two were playing golf together when MJ forced the former president to play from the furthest away tees.
"You're going to play from the little girls' tees?" Jordan asked him.
Clyde "The Glide" Drexler
When told that Clyde Drexler was a better three-point shooter than him, Jordan responded "Clyde is a better three-point shooter than I choose to be."
Ping Pong
He once lost a game of ping pong to a teammate, then proceeded to buy a table and spend the next six months practicing almost non stop.
Allan Houston
When the Dream Team lost to the college All Stars in a scrimmage, before the rematch the following day Jordan pointed at Allan Houston and said "I got him," and as the story goes, he didn't touch the ball for two hours.
Jerry Stackhouse Rookie Year
Stackhouse tells the story about his first encounter with Mike as a rookie:
-So Jerry is guarding Mike as Mike brings the ball down the court. Jerry is waiting for him on the other side of half court.
Jordan makes eye contact with Stackhouse and starts the trash talk of course
JORDAN:Which Side?

Jerry doesn't say anything back because he knows Jordan is trying to get in his head.

JORDAN: Which Side?

STACKHOUSE: Whatever man, just play ball man

JORDAN: I'm not saying what side do you want me to go by you, thats gonna happen regardless, I'm going to put you on my poster today so I am asking you what side you like of yourself and I'll make sure that when I dunk on you I know what side you want showing.
MTV VJ Kennedy
[In 1995], she was having dinner with MJ and Russell Simmons at the Bowery Bar in NYC, when Michael broke out some dice.
Before long, Kennedy says, Jordan decided it was "time to play for something"

... and said, "If I win, you come back to my hotel room with me tonight."

Kennedy says she freaked out because she was a virgin —and imagined MJ's giant penis would "eviscerate me from the inside out" ... so she asked if they could play for
Knicks tickets instead.
And that's when Jordan allegedly reminded Kennedy he had a wife — and offered her
Nets tickets as a consolation.
Cheating an Old Lady in Cards
Buzz Peterson invites Michael Jordan over to play a casual game of cards with Peterson’s mother. No money is wagered—just a simple, friendly game.
But when the old woman gets up to use the bathroom, Peterson catches Jordan trying to cheat. #hoh
Airport "Gambling"
Jordan used to bet with his teammates about everything, and one time he bet on whose luggage would come out first at the airport. What his teammates didn't know is that he had pre-arranged for his luggage to come out first with the employees at the airport, who of course were happy to do something for Michael Jordan. I hope he tipped the airport employees afterwards, but that wasn't part of the story.
g.o.a.t