With Oprah Winfrey, the intersection of politics and education is making for strange bedfellows. Federal tax returns and other reports confirm that she’s accepted at least $5 million for her self-named South African girls’ school from perhaps Barack Obama’s single greatest political enemy.
Oprah is probably the most well-known celebrity to back Senator Barack Obama’s bid for the presidency. She threw him a lavish launch party, endorsed him on her show, stumped for him in the early primaries, and cried — as captured by photographers — in a Chicago park when he won the election. Her loyalty seemed fierce.
But it turns out that Winfrey is very close friends with Dallas billionaire named Harold Simmons, a leading Republican donor and supporter of John McCain.
This past August it was revealed that Simmons was the single donor to a 527 committee called American Issues Project. Its only issue: to run ads linking Obama to William Ayers, the political activist who was once part of the Weather Underground. Simmons paid $2.9 million to try and make Ayers the Obama campaign’s “Swift Boat,” an issue that might have sidelined permanently the Illinois senator’s chances and advance John McCain — Simmons’s candidate — to the White House.
Nevertheless, Winfrey has cultivated her friendship with Simmons on many social fronts since 2001, resulting in his being second only to her in donating funds to her Leadership Academy in Johannesburg, South Africa.