But Oprah is in a class by herself. Cuban and Zuckerberg, like many famously sharp-elbowed corporate executives, are both loved and hated, while Iger lacks a household name. But Winfrey, the rags-to-riches media mogul, is one of the most famous, successful and influential people in the world, and has reached those heights while attracting relatively few harsh critics along the way. Even after she dipped her toe into politics by endorsing Barack Obama in 2008, she retained high favorability among people of all partisan stripes, even though her numbers with Republicans dipped.
She outshines Trump’s private-sector career on several fronts. Trump leveraged his daddy’s inheritance to become a billionaire, despite a sloppy management style and several high-profile business disasters along the way. Winfrey, meanwhile, survived poverty, childhood sexual abuse and workplace sexual harassment to become the world’s first black female billionaire.
The Oprah Winfrey Foundation runs circles around the Trump Foundation, and has given her some actual experience in education and housing policy. Winfrey has built 60 schools in 13 countries, including her signature educational endeavor, The Oprah Winfrey Leadership Academy for Girls, a boarding school for impoverished South Africans. (The first group of her students graduated from American colleges last year.) After Hurricane Katrina, she invested $10 million of her own money and partnered with Habitat for Humanity to build a planned community in Houston, “Angel Lane,” housing 65 families displaced by the storm. And she has donated to more than 80 charitable organizations in her adopted hometown of Chicago, whereas evidence of Trump’s charitable donations is infamously thin.