In the 1980s and ’90s, every kid in America wanted to be “like Mike.” And it’s no wonder: NBA star Michael Jordan’s games were must-watch, his Nike shoe and apparel line was massively successful, and his face was plastered on advertisements for everything from Coca-Cola to Big Macs to oatmeal. A 1998 cover story by Fortune writers Roy S. Johnson and Ann Harrington calculated the value of the “Jordan Era”—the apparel company that the NBA legend runs through Nike, his massive portfolio of endorsements, and the attention he brought to the NBA—at roughly $10 billion. 

Of course, since then, the man and his brand have generated multiples of that amount. Just 35 when he was profiled by Fortune, Jordan described wanting to step back from his intense career and spend more time with his family. But his retirement from basketball seven months later hardly slowed the momentum of his business empire. Since then, he acquired the Charlotte Bobcats (now the Hornets) for $275 million and flipped the NBA team in a deal worth roughly $3 billion. And the Jordan brand has remained a reliable rainmaker for Nike: With retro rereleases of the iconic Air Jordan shoe, it was the one bright spot for the company in its bleak fiscal 2024, bringing in $7 billion and doubling its revenue from 2020.

Indeed, one of the big challenges ahead for Nike, its new CEO Elliott Hill recently told Fortune, is to find an athlete “like Mike” to move the brand forward. “Do we have a Jordan in our portfolio?” Hill mused to the writer Devin Gordon. “Don’t know yet, but it’s our job to be planting those seeds.”

Jordan’s storied collaboration with Nike (immortalized in the 2023 movie Air, depicting the company’s wooing of the superstar) will be hard to replicate today. The “Jordan Era” was a time when there were more eyes on fewer mediums, long before the ever-increasing number of algorithms, apps, and ads began vying for our attention. As Gordon wrote, “Cultural dominance of the scale that Nike used to routinely achieve is also nearly impossible now—the global marketplace is too crowded; social media is too fractious; sports has gotten, frankly, too big.”

Jordan, now 61, played to the spotlight and became an irresistible force. Hill, Nike, and the NBA, on the other hand, are struggling to convince people to look.