Oprah Winfrey
Winfrey was a talk show host and CEO of Harpo Productions in 1989 when she was honored in Crain’s inaugural 40 Under 40 feature.
“Money may not define Winfrey, but she does make a lot as hostess of ‘The Oprah Winfrey Show,’ ” Crain’s wrote at the time. “A recent Forbes magazine listing of the world’s highest-paid entertainers ranked her 9th, with an estimated combined income of $55 million in 1988 and 1989.” Three decades later, she has a net worth of $2.5 billion.
J.B. Pritzker
Long before announcing his candidacy for Illinois governor, Pritzker was a member of Crain’s 40 Under 40. He was named in 2000, shortly after a credible but unsuccessful run for Congress. He was the managing director of William Blair New World Ventures, where he and his partners managed a $100 million pool. “I don’t think he succumbed to the dot-com mania,” a Silicon Valley executive praising Pritzker said at the time.
Chance the Rapper
In the two months leading up to the 2016 40 Under 40 feature, Chancelor Bennett, then 23, embarked on a sold-out North American tour, staged a festival at the White Sox’s home ballpark, signed on to be the face of a campaign for fashion retailer H&M and hosted a surprise get-out-the-vote concert in Grant Park.
“There were no Chicago shows—none of the venues wanted to book a hip-hop event and, even if they did, no one would come out,” Chance told Crain’s of his time coming up in Chicago. That had changed by the time he was a 40 Under 40. “Now the Chicago show is a guaranteed dollar for everybody involved.”
Nate Silver
Shortly after his dead-on forecast that the Tampa Bay Rays would contend for a division title and besting national polls in predicting the victory margins in the Democratic primaries, Silver was named a 2008 40 Under 40. The 2000 University of Chicago economics grad “looks right at home in his hipster-thick Wicker Park neighborhood,” Crain’s wrote at the time, going on to describe Silver’s FiveThirtyEight.com as a “mishmash of color-coded maps, pie charts and graphs splicing the presidential race every which way.”
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