By Erik Maza,with contributions from Samantha Conti, Evan Clark, Lisa Lookwood

Wondering what Anna Wintour wants has become a cottage industry of its own. Does she want to be a diplomat? A theatrical impresario? A grand dame? Have a broader corporate editorial role? Well, that last one may have some truth to it.

Every couple of months, someone, typically on deadline, throws out a new scenario. How about Anna to go on for Regis? And then in a matter of minutes it’s everywhere, in Mike Allen’s Playbook, on the “Today Show,” another mini story to feed the news cycle.

On Tuesday, Bloomberg News caught up with the practically fossilized rumor the White House wants Wintour to be its ambassador to the U.K. or France. The ambassador idea gained currency already in June after it was reported in two major British newspapers: The Guardian, where Wintour’s brother Patrick is a political editor, and The Independent. Then, the papers cited speculation among insiders. Later, The New York Times picked up the thread in a Styles piece.

Bloomberg was tipped by “two people familiar with the matter.”

This could have been, quite plausibly, someone in the White House, which has ample reasons to be thankful to Wintour for her role in organizing lavish dinners in the run-up to the election. Or it could have been an aide wondering out loud on the set of Bloomberg TV’s upcoming interview with President Barack Obama.
Wintour becoming a government employee — granted, one posted to Paris or London, as the rumor has it — is a turn of events as likely to happen as Hillary Rodham Clinton to Gracie Mansion, the official residence of the mayor of New York City. Condé Nast insiders say Wintour may not be all that interested in the dull intricacies of foreign diplomacy, though they speculate the administration might be considering her for some kind of political role, just not a full-time gig. Furthermore, Wintour recently signed a multiyear contract that comes with financial penalties should she leave it. But the rumor rears its head every now and then because it is mutually beneficial to all parties involved. If the source is in the administration, it allows the White House to reward a trusted political bundler with flattering press.

(On Tuesday afternoon, an ABC News blogger wrote he had confirmed the Bloomberg report, though he didn’t cite sources and concluded Wintour faces competition for the job.)

For Wintour, the speculation lends gravitas to her already burnished profile as fashion’s biggest star. A spokeswoman didn’t flat out deny to Bloomberg or WWD that Wintour would ever consider such a post. “That’s just a hypothetical question. What I know is currently, and she’s very happy with her current job,” she said.

It also doesn’t hurt that the report has surfaced just a few days before a new documentary ardently promoted by Vogue bows on HBO.

“As usual, she’s playing it beautifully. It contributes to the Anna brand, and it helps the magazine,” a source said.

It is not unreasonable to wonder what’s in store for Wintour’s autumn years. She is now 63, nearly 25 years into her job at Vogue, nearly 30 at Condé Nast, and in recent years has been trying on new roles the way her models try on the newest collections.

She has become more active politically — in 2008, she donated $100,000 to the Obama campaign, according to the Center for Responsive Politics, and was on her way to becoming a top bundler (donors who wrangle other VIPs for a campaign). In this cycle, she organized several lavish fund-raising dinners in Obama’s honor and, according to Bloomberg, raised more than $500,000 for the President — not to mention spearheaded a fashion industry product initiative that Fortune calculated raised $40 million for Obama. And she has become an informed citizen, concerned not just about Democratic congressional candidates — she gave Bob Kerrey $5,000 for his Nebraska Senate run, according to the Federal Election Commission — but also social causes like gay marriage.

It was noted by some that given Wintour’s extraordinary fund-raising efforts, “there should be some payoff.”

But Oscar de la Renta, one of Wintour’s closest friends, said, “When you are editor in chief of an extremely successful magazine, you don’t need an ambassadorship for four years. Ambassadors were great in the 18th century. Today, it’s going to the opening of a cafeteria.

“She should be named Secretary of State. That would be a different story.”

De la Renta said he’s absolutely sure Wintour would never leave her job at Vogue. He said becoming an ambassador requires deep pockets — at low pay, since the average ambassador’s salary is $179,000 a year — and they spend a lot of their own money. He hasn’t discussed it with her, but he thinks the idea is ridiculous.

Then there is the reaction her appointment would get in London or Paris.  In London, the British press reacted to the Bloomberg speculation either by poking fun at any potential appointment or by playing the story straight. (Anecdotally, many Britons think the U.S. system of appointing major political fund-raisers to plum ambassadorial posts is unfair, and that the jobs should go to seasoned diplomats, as it does in the U.K.)

The Daily Telegraph believes Wintour would easily knock her putative rival — another top fund-raiser, Matthew Barzun — out of the way. “Did he deliver dinner at Sarah Jessica Parker’s apartment with Meryl Streep and Aretha Franklin? How about dinner at Hollywood mogul Harvey Weinstein’s house with Gwyneth Paltrow, Alicia Keys and Quentin Tarantino?” wrote Belinda White.

“Is this Barzun character BFFs with Roger Federer? Does he have Karl Lagerfeld on speed dial? And that’s before we even get into the wardrobe.”

The Evening Standard took a more straightforward approach, pointing out that, if appointed, Wintour would follow in the footsteps of Pamela Harriman, who was picked for the plum role of U.S. Ambassador to France.

The ambassador’s role in the U.K. is a malleable one, and each individual puts his or her own stamp on it. Joseph P. Kennedy Sr. famously used the post to scale the heights of British society —marrying his daughter Kathleen “Kick” Kennedy off to the Duke of Devonshire’s eldest son and the heir to Chatsworth.

More recently, Robert H. Tuttle — appointed by George W. Bush — and his wife Maria Tuttle were huge contemporary art fans and utterly gregarious hosts, throwing open the doors of Winfield House — the ambassador’s official residence in Regent’s Park — to mark holidays or big London events.

The current ambassador, Louis B. Susman — who has already revealed plans to step down — has been competent and diplomatic but far less fun. He and his wife, Marjorie, have preferred instead to keep the public — and the press — at arms’ length.

“Being nominated and serving as the Ambassador of the Court of St. James’s is one of the highest privileges the President could bestow on an individual,” said Louis Susman’s son William, managing director of Threadstone. “The requirements of the post are very demanding and require a broad set of skills of which I’m confident the administration will identify numerous qualified candidates.”

The U.S. ambassador in London is an important surrogate for President Obama in the U.K. and can be called upon to weigh in on important topics of the day, from defense and security issues to cultural and economic ties between the two countries.

So if Wintour doesn’t become Madame Ambassador, what might be next? She clearly has taken editing Vogue far beyond just running a magazine and may want to do more than organize Fashion’s Night Out, the CFDA/Vogue Fashion Fund, the Costume Institute gala and similar activities. She has been involved in the theater, endowing since 1999 an awards event in London in honor of her father, Charles, the former editor of the Evening Standard.

Wintour is also keen on keeping her strong relationship with Hollywood. In late October, she was spotted lunching with Condé Nast Entertainment’s Dawn Ostroff at the Beverly Hills Hotel. Representatives for both declined to comment on the subject of the sit-down.

Then there’s always her current perch: The one place where she’s been courted in no uncertain terms for a long future is Condé Nast. Sources say executives want her to not just stick around at Vogue, but to eventually play a larger role in the company in coming years, possibly stepping into the kind of creative director position once filled by Alexander Liberman. Though few possess Liberman’s visual eye, his was a role Wintour was intimately familiar with. After getting snatched up from New York in 1983, Wintour diligently sought Liberman’s approval during her stints at British Harper’s Bazaar and House & Garden, going so far as to send him dummies of her layouts. Once she landed at Vogue, she continued paying her respects by asking for his advice, but his input was gradually phased out as she developed her own voice.