A decade after retiring as a basketball player, Michael Jordan spends his time playing golf, losing tons of money gambling on Caribbean islands, and half-steering the worst team in NBA history. In the meantime, he banks $60 million a year primarily because people riot like clockwork outside Foot Locker for the right to buy his $180 retro sneakers. The shoes, which make up the primary component of his brand, still look as good as ever.
Jordan himself, on the other hand, has not aged particularly well. Long removed from the fine Italian tailoring he’d wear to games in his playing days, the Jordan evokes a man awkwardly trying to appear younger, donning ridiculous ripped stone-washed jeans and suits your creepy uncle might wear to courtside appearances. Jordan’s hypercompetitive nature, long romanticized when he used to suit up—even when he’d punch a teammate—is even more ill-fitting: Without games to play, he’s an outgrown version of the high school jock who can’t seem to let go of his glory days. (Witness his awkward, vindictive Hall of Fame induction speech, during which he shot verbal slings at all the adversaries he’d constructed in his mind.)
There’s no better tangible representation of Jordan’s perpetual inability to get with the times than the wretched state of his NBA team. After an uninspiring tenure running the Washington Wizards, Jordan bought a controlling interest in the Charlotte Bobcats and makes the team’s basketball decisions. The Bobcats have one winning season in his six years pulling the strings and just concluded a season in which they won seven games and lost 59, resulting in the worst winning percentage of any team in NBA history. Their terrible record ensures a high pick in the upcoming draft, but His Airness is known for botching his selections, and no player short of Jordan in his prime could drag the club out of the basement.
Plausible theories have begun to surface about why the greatest basketball player of all time seems thoroughly incapable of developing a team that isn’t horrendous. Charles Barkley, a longtime friend, thinks Jordan has surrounded himself with too many yes men afraid to tell him when something is a terrible idea. The hope is that newly-hired GM Rich Cho will once in a while have the guts to let the living legend know he has no idea what he's doing, but time will tell.
The roots of Jordan’s executive incompetence precede his legendarily bad run with the Bobcats. Jordan’s infamous 2001 selection of high school manchild Kwame Brown first overall when Jordan was with the Wizards is often cited as his biggest mistake—especially considering four-time All-Star Pau Gasol went two picks later. It wasn’t even so much that Brown was untalented, but more that he had the mentality and temperament of a 12-year-old. Jordan, who as a player had open disdain for the younger generation “mentored” Brown by systematically destroying his confidence, reportedly via a constant stream of homophobic slurs in front of the entire team. Such fragile talents can develop into their potential—witness Kobe Bryant, who averaged seven points per game his rookie season—but only with requisite patience and guidance, neither of which Jordan gave Brown.
Past that, one has to wonder whether someone like Jordan could help being at least somewhat warped. A long way from his middle-class North Carolina upbringing, Jordan reached—and in many ways remains at—the global icon level, a stage of fame so massive it all but unhinges one’s grip on reality. To most of the world, he’s less an athlete than a basketball-playing Michael Jackson. No longer the best in the world at what he does, but eternally drunk on his own Kool-Aid, Jordan has never figured out that the best thing for him to do would be to surround himself with smart people to run the show, stay the hell out of the way, and reap the rewards.
What’s hardest to reconcile is Jordan’s apparent lack of drive as an executive. A naturally talented player, he became indomitable due to his tireless work ethic—few guys that good bother to work that hard—but that hasn’t carried over to the teams he runs. (If he spent more time in the office, he’d have easily seen how good Gasol was, or that 2006 No. 3 overall pick Adam Morrison was as terrible as his mustache.)
And yet, unease over Jordan’s loss of mystique is far more our issue than his; he was the avatar of basketball when we were young, so it’s comforting to think he’s still dominant. (In certain ways, that holds; his ubiquitous logo graces nearly every decent-looking basketball sneaker sold.) If a wildly wealthy Jordan wants to take it easy, wallow in his bitterness, and phone it in on the job after 25 years outworking the industry, that’s his prerogative—though that’s not much consolation to Bobcats fans, if any still exist.