Since investing in the Chicago Sky in 2006, singer Michelle Williams of Destiny’s Child fame has sung the national anthem at multiple games, joined a Sky star in a photo-op with local high school players, hung out with fans at a meet-and-greet — and, of course, enjoyed the best seats in the house.

With her minority stake in the 2021 WNBA champion team, Williams belongs to an exclusive group of pop stars who own a slice of a sports team, including Usher, J. Cole, Pitbull, Fergie, Marc Anthony and Justin Timberlake. And with the Sky recently valued at $85 million, her investment is paying off in multiple ways.

“It checks a lot of the boxes — [she] is from the city, a fan of the sport, a woman, a member of an iconic group,” says Jonathan Azu, founder and CEO of Culture Collective, which manages Williams. “It has the hallmarks of why you would do something like that: ‘I’m associated with this team, so it brings a lot of value to my brand.’ ”

For an artist, that kind of value is both figurative and literal. Whether it’s Usher buying a small stake in the NBA’s Cleveland Cavaliers, Anthony and Fergie becoming minority owners of the NFL’s Miami Dolphins, Cole buying into the NBA’s Charlotte Hornets or Pitbull becoming co-owner of NASCAR’s Trackhouse Racing Team, money is a primary motivator.

“The stock market can go down, but the value of, say, the Texas Rangers is not going to go down,” says Michael Rapkoch, founder and CEO of Dallas-based Sports Value Consulting. Usher’s $9 million Cavs investment, for instance, may have more than quadrupled in value since he first made it in 2005, according to Forbes estimates. “I’m very happy to say that I don’t just have a basketball team, I have a championship team,” Usher tells Billboard, noting the Cavs won in 2016 under his watch. “That legacy is associated with something that I made an investment in.”

Perhaps the best-known artist-turned-team owner is Jay-Z, who spent $1 million on a small stake in the NBA’s Nets in 2004, helped move the franchise from New Jersey to his native Brooklyn, then divested from the team in 2013 to avoid a conflict of interest with his Roc Nation Sports agency. His windfall from that deal, according to Forbes, was an estimated $1.4 million.

Investing in a team can also mean easy self-marketing. When Timberlake, whose investing group owns a reported 2.8% of his hometown NBA team, the Memphis Grizzlies, played camera operator at home games, Sports Illustrated covered the story. “Sports is entertainment. There is crossover at every level,” Mark Cuban, who recently sold his majority stake in the NBA’s Dallas Mavericks for a reported $3.5 billion, tells Billboard.

That said, even a minority stake can be risky — “no different than any business,” as Cuban says. “If it’s not well run [and] customers aren’t happy, you can lose a lot of money.” That’s why none of longtime Bay Area music business manager Tim Jorstad’s clients have ever bought stakes in teams, even though many of his clients, which include the Doobie Brothers, Jefferson Airplane and members of Journey and the Grateful Dead, are regional sports fans.

Nonetheless, the perks tend to outweigh the potential downside for artists craving a piece of the sports pie. “It’s a fun investment. [Artist-owners] go to a lot of games and get to sit in the owners’ box and go onto the field and schmooze,” Jorstad says. “There are very few other normal investments where you get that kind of public exposure.”

Additional reporting by Gail Mitchell.

This story will appear in the Feb. 10, 2024, issue of Billboard.