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Michael Jordan looks on as he addresses a press conference ahead of a match between Milwaukee Bucks and Charlotte Hornets in Paris in January, 2020.FRANCK FIFE/AFP/Getty Images

Less than a year ago, you’d have said that Michael Jordan’s postplaying career work has been a bit of a fizzle.

Not a bust, certainly. Most successful pros end up owning some real estate or a chain of tacky sports bars. Jordan owns an NBA team and has his own billion-dollar brand under the Nike banner. He is far and away the most successful businessperson of his cohort.

It was a fizzle because Jordan had taken his public capital – probably the most ever accumulated by an athlete – and turned it into nothing.

He was, at best, a cipher. A guy in a suit. When you thought of his life after the glory days ended, the story that leapt to mind was Kwame Brown.

After the second of his three retirements, Jordan was named president of the Washington Wizards. His most notable decision was pushing the team to draft Brown, a high-schooler, first over all.

Brown was more than a bust. He was a bust for the ages. It was later reported that Jordan was more than a little responsible for that, first as an executive and then, once he’d unretired, as a teammate. He’d apparently ridden Brown like a mule, destroying the teenager’s confidence.

Whether the worst of it was true (Brown later denied the most incendiary specifics), the impression stuck. Jordan was recast as a bully and a misanthrope. He flamed out as a basketball executive, then receded from public life.

His commercial prospects continued to thrive. But while his closest peers – the Magic Johnsons, Larry Birds and Reggie Millers – remained integral to the sports conversation, Jordan became the rich guy who lives in the spooky mansion on the hill. Nobody ever heard from him and everyone was a little scared of him.

Now, all of a sudden, Jordan’s all over the place. Twenty-some years removed from being the most famous person alive, he’s the new breakout star of COVID.

On Monday night, Jordan announced he’s bought a NASCAR team. Which is, I suppose, the sort of thing you do when you’re worth a couple of billion dollars.

The new team’s driver is Bubba Wallace. You will remember Wallace from the ‘noose in the paddock’ story that consumed the news cycle several years ago (or maybe just last June, because we are all now ageing in whatever the opposite of dog years is).

So the only Black majority-owned NASCAR team will feature the circuit’s only Black driver, just a few months after a racial set-to featuring that driver caught global media attention.

I’m getting a picture of how this negotiation must have gone:

Jordan: “I’d like to propose that …”

NASCAR: “Yes.”

Jordan: “I haven’t said what I’m ta…”

NASCAR: “Absolutely.”

Jordan: “But how do you kn…”

NASCAR: “Free. Whatever you want is free.”

At the outset of this season, Wallace had secured sponsorship for less than half his races. In the wake of the noose controversy, he has been overrun with corporate offers. Since announcing his intention to resign from his current team, Wallace has been guaranteed millions of sponsorship dollars that are attached to him personally.

That’s not how this works. The big money attaches itself to the team – the Ferraris and Hendrick Motorsports of the world – while drivers come and go.

A few of them – Michael Schumacher, Dale Earnhardt Jr. et al – win so much they become their own brands. But that process is supposed to take years.

Wallace has turned the idea on its head. He’s a rainmaker despite not having won anything.

So if it is possible to buy a sure thing in sports, Jordan just managed it. Between the good press this brings a sport on the racial ropes and the money that comes attached to his newbie driver, there is zero risk of any sort here for the principal. Even if Jordan ends up losing, he’s already won.

We know Jordan likes to win – likes it more than you like anything – because of The Last Dance. In retrospect, that remarkable Netflix docu-series looks less like Jordan’s confessional and more like his re-emergence into public life.

A lot of people didn’t like the Jordan they saw there – obsessive, grudge-holding, still embittered by ancient and minor slights. At least, that’s what they said out loud on the internet because … he was honest? He didn’t pander? I’m not sure why.

There’s almost never been a bad time to be rich and famous. But outside of St. Petersburg in 1917, we’re getting pretty close to it right now.

However, the passage of time and the changing of fashion offered Jordan a chance to do something that was not possible when his face was on every other billboard on Earth – to appear transgressive.

Jordan the Grinch, Jordan the Winner at All Costs, Jordan the Man Who Does Not Care What You Think of Him. That now seems like a new and exciting sort of celebrity. One who doesn’t spend half his life on social media telling people what to read or how to think. Instead, leveraging his enormous wealth, he just does.

Jordan is Jeff Bezos or Bill Gates, but glamorous. He can be a fairy godfather to whatever cause he wants. The guy who once said that Republicans buy sneakers too can donate US$100-million to Black causes, and he doesn’t need it to be a PR win. He can do it just because he wants to. He can buy a NASCAR team because that seems cool, too.

The Jordan who destroyed Brown, the Jordan who owns a racing team and the Jordan who does philanthropic good works need not necessarily be different people. All of them want to win.

Deep in the thick of middle age and after years spent avoiding public life, perhaps this Jordan has just slightly recalibrated what he would like to win at.