These days Michael Jordan is known as the blueprint for on-the-playing-field dominance and business acumen. What many may not remember is that it has been like that nearly since the moment he left Dean Smith’s comfy Chapel Hill domain to enter the muddy waters and bright lights of the NBA. In 1986, MJ was only 23 years old coming off an shortened season due to a broken foot, but also his now iconic 63 points playoff performance in Boston Garden. While preparing to watch those same Celtics and the Houston Rockets square off in the Finals, he also stopped by David Letterman’s then-NBC show for this hilarious and vintage interview.
MJ, in his finest ’80s gear, donned a shiny suit which would even make a 1997 Puffy envious and showcased a still humble, yet engaging personality. Endorsements were not foreign during this era in sports, but even the normally witty Letterman was taken by surprise with Mike’s laundry list at such a young age. Sneakerheads will shed tattoo tears of joy over the discussion of the first two Air Jordan prototypes and even raise eyebrows over Jordan’s dislike of the first shoe.
The most intriguing part of the interview, however, was Jordan’s revelation of wanting to retire at age 32 and join the PGA Tour. This means he would have retired in 1995 and it may have very well happened had that Pippen trade actually gone through. Thankfully, the story is now common knowledge: he retires in 1993 to play baseball–not golf–only to return in 1995 further cementing his legacy with an eventual second three-peat.