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When President Barack Obama hosted dozens of his top donors at the White House in late November for a celebratory postelection dinner of chicken and pumpkin pie, few in the room could claim to have done more to elect him than Anna Wintour, the editor of Vogue magazine.
And after raising millions of dollars for Obama, Wintour had a prize in mind, according to several people close to the White House: appointment as ambassador to the United Kingdom, the United States' most prestigious diplomatic post.
But by the time Wintour returned home to New York, officials had told her the job in London would almost certainly go to someone who had done even more for Obama: Matthew Barzun, a genial former technology executive who spent 20 grueling months as finance chairman of the president's national fundraising operation.
As Obama begins his second term in the White House, the donors and bundlers who raised more than $1 billion to get him there are pressing hard for appointments. The sheer scale of Obama's fundraising machine has led to an especially intense scramble for plum ambassadorships, with as many as 300 people vying for 30 or so positions, according to several people involved in the process.
''The president now has six years of relationships, not two years," said Andy Spahn, a public relations and political consultant who, along with film producer Jeffrey Katzenberg, was Obama's top Los Angeles fundraiser. "So I expect that it will be a lot more competitive this time around."
Interviews with more than a dozen donors, Democratic officials and advisers involved in the discussions revealed some unspoken rules: Volunteer for more than one country. Be prepared to serve for only two years, so that a second round of envoys can be appointed before Obama leaves office. Don't mention how much money you raised for the campaign (but don't expect much if you didn't raise at least a million dollars). Let it be known where you want to go but don't publicly campaign for the job.
"You have to find the balance between waving the flag to get your name out there and waving the flag so much you smack people in the face with it," said Jonathan Prince, a former State Department official under Obama.
Nearly every aspiring ambassador contacted for this article did not return phone calls or declined to comment about any interest in specific jobs. But speculation about who is in line for what often makes its way into the media. Last month, The Hollywood Reporter published the names of several West Coast donors said to be on Obama's short list for diplomatic posts — a list as closely scrutinized by Hollywood for who wasn't on it, other donors said, as for who was.
''You are talking to the only person in Hollywood who isn't asking for one," Spahn said.
For some would-be diplomats, the hunt began the day after Obama's re-election in November, when the president's top aides began asking his leading fundraisers if they had interest in serving. Barzun has been an informal facilitator for donors and fundraisers, along with Rufus Gifford, his counterpart on Obama's campaign staff. Inside the White House, a small group of senior aides — including counselor Pete Rouse; Valerie Jarrett, a senior adviser; deputy chief of staff Alyssa Mastromonaco; and Obama's personnel director, Nancy Hogan — have met regularly to discuss potential choices.
Obama has followed recent tradition in making appointments; like every president going back to Ronald Reagan, he has filled about 70 percent of the posts with career diplomats and 30 percent with political appointees, often but not always top donors. Dangerous spots like Yemen are invariably filled by diplomats, according to statistics compiled by the American Foreign Service Association. Highly sought European and Caribbean countries usually go to political appointees. At least three Obama fundraisers are interested in Italy this time around, according to people familiar with the roster of potential candidates. They include Azita Raji, a San Francisco philanthropist; John R. Phillips, a Washington lawyer married to former Obama aide Linda Douglass; and Robert Mailer Anderson, a novelist.
But Asian countries are increasingly desirable. Steve Westly, a California venture capitalist and top Obama fundraiser, has discussed with administration officials the ambassadorship to China, among other jobs, according to people with knowledge of the talks. The post is currently filled by Gary Locke, a former commerce secretary, who may depart later this year.
Deep pockets are an unofficial requirement for many postings. While ambassadors earn a maximum base salary of $179,700, and housing is provided with the job, in some capitals they can expect to spend hundreds of thousands of dollars a year on entertaining. So those who can "self-finance" have a competitive edge.
The expectation is so ingrained that Timothy Roemer, a former congressman, felt compelled to bring up his bank account when Obama named him ambassador to India.
''I told the White House and the State Department early on, I can't afford to do the job like that," Roemer said.
Not everyone wants a gilded posting in a European capital. Ellen Susman, a Texas philanthropist who contributed $100,000 to the super PAC supporting Obama, has alerted people involved in the decision-making of her interest in serving as director of the State Department's Art in Embassies program, responsible for managing the art collection that hangs in U.S. embassies around the world. (Susman declined to comment.) Others are more interested in policy positions within the State Department or elsewhere in Obama's administration.
''There are some people who just want to be an assistant secretary of state for Latin America or something," said Robert Rizzi, a partner in the Washington office of O'Melveny and Myers, one of several law firms that help clients navigate background checks for high-ranking jobs.
Most presidents, Obama included, seek to find ambassadors who have business or personal ties to a nation. Philip Murphy, a former national finance chairman of the Democratic National Committee who is the ambassador to Germany, ran Goldman Sachs' Frankfurt office for four years and is fluent in German.
''In my view, some of the best ambassadors and some of the worst ambassadors have been political," said John Podesta, who ran Obama's transition team in 2009. "They have close connections to the president and are understood to be close to policymaking decisions." But those who "think they're entitled can cause problems in a bureaucracy that needs to respect foreign service officers."
Cynthia Stroum, for example, a major Democratic fundraiser whom Obama named ambassador to Luxembourg, resigned in January 2011 — one month before the State Department's inspector general released a scathing assessment of her "aggressive, bullying, hostile and intimidating" management style.
The sheer number of names in Obama's hat this year means that most will end up with nothing. Some will be offered a semidesirable country that they are unlikely to accept, a move that allows Obama's team to satisfy their donors without actually hiring them.
Other postings depend, musical-chairs-style, on what people further up the food chain do. Barzun will get the United Kingdom post if he wants it, according to several donors and advisers with knowledge of the discussions inside the administration. Wintour was a potential candidate for France but is no longer seeking the appointment, they said — which could clear the way for Marc Lasry, a successful hedge fund investor who was one of Obama's staunchest defenders on Wall Street and is seeking the same posting.
A spokeswoman for Wintour said she was happy with her job at Vogue. Lasry declined to comment.