Her ability to bundle large sums of money for the politicians she supports may be reward in and of itself. Long before Wintour was billed as one of the top fundraisers for the Obama campaign, she donated money to senatorial runs for Hillary Clinton and Kirsten Gillibrand and to Senator John Kerry's run for president in 2004. Wintour has also lent her influence to efforts to legalize same-sex marriage in New York and to the fashion industry's fight against HIV and AIDS in the early '90s.
"I don't think this is about her interest in politics," said J.Crew's Mickey Drexler, who attended the $40,000-per-plate fundraising dinner Wintour threw for Obama at Sarah Jessica Parker's New York home last week. "I think this is about her interested in taking on something she believes in. And when she takes something on, she does it with a great amount of ferocity."
Some political experts are concerned that being linked to Wintour — and the glamorous people she knows — may tinge Obama's campaign with the same kind of criticism other politicians have garnered.
"It is always a worry: how is this going to play in Peoria?" said Anita McBride, chief of staff to former First Lady Laura Bush and an adviser to three Republican White Houses. "Look at Nancy Reagan. She got vilified for having Betsy Bloomingdale as a friend and for wearing Adolfo."