Michael Jordan is the greatest basketball player ever to walk the planet, and one of the most notorious competitors in the history of sports. MJ famously punched Steve Kerr in practice and would fight to the death in a game of ping pong if it came down to it.
Jordan did take one extremely L he’s probably still thinking about. The backstory is that Jordan used to put on a $15,000 a head ‘Flight School’ fantasy camp for business execs, and as part of the experience would crush any takers in one-on-one. Jordan was undefeated over 8 year of running the camp until he met his match in the form of 45-year-old mutual fund CEO John Rogers, Jr.
Rogers was unfazed by Jordan’s vintage trash talk – and MJ did talk a lot of ish – and caught his airness slipping in the game to 3. You know this had to piss off Jordan deep down, and to add insult to injury comedian Damon Wayans was in attendance to rub it in.
This video emerged in 2008 before the ‘Crying Jordan’ meme or Twitter. Before it was released it was only a second hand legend. You could say it’s the original crying Jordan. Rogers did play point guard for Princeton in college, so it’s not like he was just some total scrub. Still, watching his airness get taken down by a balding 45-year-old CEO is incredible.
h/t Adam Warlock