For those of us who were sentient when Michael Jordan was winning basketball championships, seeing his face become a mocking emblem of sadness and incompetence has been jarring. Photograph by Stephan Savoia / AP

In 1991, Gatorade released its first commercial starring Michael Jordan. In the minute-long ad, shots of Jordan on the basketball court are spliced with those of kids imitating his signature moves, while a new earworm of a song, written specifically for the commercial, plays in the background. “If I could be like Mike,” a chorus of children's voices sings, serving as a proxy for people of all ages everywhere. Jordan had already been appearing in national ads for years, but this was his coronation.

­Michael Jordan’s athletic greatness was obvious then and remains so now. But his charm, a quarter century later, has become tougher to recall. It’s there, though, in the final seconds of the Gatorade commercial, when Jordan lifts his eyebrows, rolls his eyes, and turns, smirking, away from the camera, as if recognizing the essential strangeness of just how famous he had become. This was an early version of the Jordan Shrug, which was enshrined into sports lore the following year, during the first game of the N.B.A. Finals. Jordan made six three-pointers in the first half of the game and, after hitting the last one, he looked to the sidelines, turned his palms upward and shrugged his shoulders, pretending to be baffled by what he'd just done. Don't ask me why I'm so good, the gesture said: you figure it out.

It has become difficult to separate Jordan from the images of him that were sold to consumers. But he was no marketing cipher. The things that advertisers said were cool about him were actually cool: the wagging tongue; the acrobatic leaps; the clutch shots on the biggest stages; the shining, perfectly round bald head; the deadpan sense of humor and easy smile. The Jumpman logo that adorns his sub-brand of Nike shoes and apparel? He could really jump like that.

Last year, Gatorade revived its "Like Mike" campaign with a series of ads. Jordan made an appearance in the last one, announcing to the world that he’s "still got it." From a marketing perspective, though, that no longer rang true. Jordan had somehow lost his lustre as a pitchman—not because, like other athletes in retirement, he had done some unaccountable or unforgivable thing. The change had taken place gradually, practically invisibly. Michael Jordan was no longer cool.

If you’ve spent any time on the Internet recently, there’s a good chance you’ve seen an image of Michael Jordan’s tearful face superimposed on someone else's body. The meme, known as Crying Jordan, has been around for several years, but became ubiquitous on the Web starting this past fall. Whenever someone—an athlete, an actor, a politician—fails in a public way, his face will promptly be replaced by Jordan's. When Donald Trump lost the Iowa caucuses, he became Crying Jordan. When the quarterback Cam Newton lost the Super Bowl, he became Crying Jordan. When Michael Jordan himself, sitting in the stands at the N.C.A.A. men's basketball championship, watched as his alma mater North Carolina lost to Villanova, he became Crying Jordan. (The meme also works on non-human objects, like taco bowls.) At this very moment, someone, somewhere, is failing, and Crying Jordan awaits.

For those of us who were sentient when Jordan was winning championships, seeing his face become a mocking emblem of sadness and incompetence has been jarring. Jordan never lost when it counted, and even during his strange baseball interlude, few dared call him incompetent. But today, Crying Jordan is one element in a much broader repositioning of Jordan's place in the culture. The tearful face evokes other uncool moments from Jordan’s long career: his awkward return to the N.B.A. in the early two-thousands; his inauspicious ownership of the Charlotte Hornets franchise; his stubbornly unevolved fashion sense. Of his clothes—enormous shirts, terrible sweaters, and wide-legged, acid-washed jeans—the critic Wesley Morris once wrote, "I actually feel bad because he really doesn’t know. And I don’t know that there are many people who would have the heart to tell him to burn those pants."

The Crying Jordan image itself, as the Wall Street Journal noted in February, dates back to 2009, when Jordan gave a speech at a ceremony marking his induction into the Basketball Hall of Fame. The connection between that speech and the meme it helped spawn is important. Hall of Fame speeches are, generally, warm and generous—former players looking back fondly on legendary careers. But Jordan took a different approach. After crying briefly at the beginning of his remarks, Jordan re-litigated, one by one, individual battles he had fought with coaches and Bulls executives over the years, focussing his speech on the people who had doubted him or threatened his success. He was bitter and aggrieved, and even his jokes had a hard edge. For a player famous for his on-court grace, the speech was anything but. It was also, for many people, the most that they had heard Jordan say about himself and his years in basketball. Where was the affable hero of "Space Jam" and Wheaties boxes?

Even before Jordan gave his Hall of Fame speech, people had begun to reappraise him. In the years after his final retirement, his fierce competitiveness started being remembered more than his otherworldly ability. The stories made the rounds: how he punched a teammate in the face during a practice, how he belittled less-talented peers. There were reports of his competitiveness on the golf course, at the casino, or in seemingly any other venue of male contest. To be “like Mike” was, suddenly, to need to win. And it was forgotten that the world had fallen in love with him before he’d won all those championships. He had been marketed and absorbed and appreciated not as a ruthless competitor but as a kind of superman, aspirational not for his victories but for the astonishing fact of his very existence.

Yet even marvels grow old. In 2013, Wright Thompson, of ESPN, profiled Jordan as he approached his fiftieth birthday. Thompson presented Jordan as a lonely man—a compulsive competitor with nothing left to compete for. He was more than a decade removed from the game, and a good thirty or forty pounds heavier than his playing weight, but he still sized up the likes of LeBron James as if he might, given the chance, be able to take him. This was the Michael Jordan that members of younger generation, who never saw him play, recognized: chomping cigars, out of touch, watching games high up in his executive suite. Of his fierce competitiveness, Jordan told Thompson, "It's consumed me so much. ... I'm my own worst enemy. I drove myself so much that I'm still living with some of those drives." This Jordan was almost a tragic figure, and it helps explain the Crying Jordan meme: if you can’t win anymore, you can only lose. The image of blubbering Jordan is part despair, and part tantrum. The meme is the people knocking Jordan down several pegs. Jordan in his prime was unassailable, a man out of reach, way up there above the rim. Now even you can take him.

The further we get from Jordan's playing days, the easier it is to believe that he was just a marketing mirage. This is partly his doing, even if it’s not his fault. While he almost certainly never said "Republicans buy sneakers, too”—as is often attributed to him to explain why he remained mostly aloof from politics and quiet on social issues—he has always been a meticulous curator of his public image, and a vigilant protector of his right to earn money from his likeness. (There's even mild concern on the Internet that Jordan, Inc., might soon try to come for Crying Jordan.) It’s ironic, too, that, as the man himself becomes inevitably less cool, the sneaker brand that bears his name has become only more sought-after and fetishized, to the point that “Jordan” and “Jordans” mean very different things. Just last summer, Jordan fell victim to a different Web meme while taking questions from kids at a basketball camp. In a gymnasium packed with young people, a camper popped up and shouted "What are those?" at Jordan, mocking the legend’s new sneakers. The entire place erupted in laughter. Getting owned by a seventeen-year-old: the world must seem like a strange place to Michael Jordan these days.

A new generation of basketball fans knows only this earthly, diminished Jordan, and it seems to have decided that he holds up poorly compared to the man who now claims the title of best player on the planet: Steph Curry. Curry, like Jordan in his day, represents a step forward in the evolution of basketball. And he is the centerpiece of a team that not only wins a lot of basketball games (the most ever this season, surpassing Jordan's 1995-1996 Bulls) but appears to have a great deal of fun doing so. It's impossible to imagine Curry punching a teammate in practice, or mocking the lesser players on his team. Curry radiates only joy, which, for now, seems as though it will last forever. Of course, Jordan was young once, too.

“I think eventually people are going to recognize the crying Jordan face more than his actual legacy,” a real twenty-four-year-old person told the Wall Street Journal earlier this year. Please, put a Crying Jordan face on that millennial. And then put one on me, and on everyone else.