During the beginning of Michael Jordan 's NBA career, he was likely able to still do some of the stuff that he had gotten used to doing when he wasn't that famous. But it didn't take him long to become a household name in Chicago , and, as a result, going out had become a struggle for the Chicago Bulls icon.
Former teammate Brad Sellers once wondered how Jordan managed to eat or go grocery shopping without attracting too much attention. Apparently, Jordan struck a deal with a local Jewel-Osco branch. He would arrive about 15 minutes before the shop closes, and the shop would accommodate him even after operating hours. To repay the staff for their kindness, he reportedly gave out generous tips, impressing Sellers.
"He wasn't making no $30 million a year; I'm sure at that time he was making less than a million," Sellers said . "But it was a lot of money at the time, and he made sure that he took care of people."
MJ's inimitable generosity
Jordan's proclivity for making other people's days with lavish tips is well known. Some might think that it's easy for him to hand out thousands of dollars, as such amounts are just chump change for the world's first billionaire athlete .
However, Sellers' story provides a different picture of Jordan's benevolence. The retired power forward didn't specify exactly when the tale occurred, though we can infer it happened between 1986 and 1989, since his tenure with the Bulls spanned that period. At that time, Jordan's salary had yet to exceed $1 million per season. Even so, he didn't appear to hesitate to take care of people, as Sellers put it.
What transpired is aligned with what we've heard and read about "His Airness" over the years.
People from different walks of life who have worked for and with him have said the same things about his generous tipping. Of course, there may have been times when his frugality took over, such as when Wayne Gretzky called his friend out for offering a gratuity of just $5 dollars during a night out in Las Vegas . But that may have been an exception to the rule for the five-time NBA MVP.
Becoming a beloved figure in Chicago
Jordan's goodwill toward Chicago helped him become one of the most beloved athletes in the city. Well, it also helped that he put the Bulls franchise on the map by transforming it into a perennial contender and bringing the championship trophy there not just once, but six times. If you ask around which sports figure is most associated with the Windy City, chances are, Michael's name will be mentioned first before Chicago natives, including Isiah Thomas and Dwyane Wade .
It has been nearly three decades since we last saw Jordan in a Bulls uniform, and yet, his presence can still be felt throughout Chicago. For many longtime residents, including those who have benefitted from his generosity, he was more than just a basketball player. He represented a level of global recognition that Chicago sports had experienced before his arrival.
Anecdotes like Sellers' may not be as consequential as Jordan's game-winning shots or the six championship parades the Hall of Famer helped bring about. Still, it explains well why he became beloved beyond basketball circles.
This story was originally published by Basketball Network on May 26, 2026, where it first appeared in the Off The Court section. Add Basketball Network as a Preferred Source by clicking here.

