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In October of 1969, Vincent de Roulet, the newly appointed ambassador to Jamaica, arrived in Kingston aboard his 90-foot yacht, soon to be joined by 17 of his race horses. Wealthy by birth as well as by marriage (his wife was a Whitney), the 44-year-old dilettante had no experience in international diplomacy, his résumé instead boasting a variety of club memberships, horse-racing activities, and board service for various Long Island hospitals.

But de Roulet had grown bored with his posh life in New York — “sitting around the club simply complaining about things,” he told Harper’s in 1974 — and thought it might be nice to instead serve his country as an ambassador. So following longstanding American tradition, de Roulet donated $75,000 to Richard Nixon’s election campaign, vaulting him ahead of dozens of career foreign service officers and landing him the appointment to Jamaica, which had recently won independence from England, in 1962.

Fancying himself a man of action, de Roulet immediately chafed at the traditional strictures of diplomacy and set to work shaking things up. (“You have to remember that until I arrived, Kingston used to be the repository of the dregs of the Foreign Service,” he told Harper’s.) His disdain for the State Department employees beneath him also extended to Jamaicans, to whom he publicly referred as “idiots” and “children.”

One of de Roulet’s primary initiatives was to revamp visa processing. For years, Jamaicans had been routinely granted tourist visas to get to the United States, where they frequently remained illegally. As a remedy, de Roulet limited the number of visa seekers and screened them aggressively, forcing applicants to queue up well before sunrise to get into the embassy. Then, he closed off the building’s restrooms for visa applicants, telling a Rotary Club luncheon that “Jamaicans take pleasure in flooding our toilets.”

De Roulet was arguably the worst ambassador to have bought his position during Nixon’s profligate presidency, but the selling of ambassadorships has long been a major subsidiary of the bipartisan quadrennial bazaar known as “the buying of the president.” As the 2008 general election campaign picks up and the campaign money flows, there is no way to know which big donors will become ambassadors in a McCain or Obama administration — at least not till after Inauguration Day in January, when nominations will be in order.

It’s difficult to know how many ambassadorships were sold before the Nixon administration’s egregious corruption inspired reforms that started putting campaign contributions on the public record. But researchers can trace how many ambassadorial appointments went to career Foreign Service officers and how many went to political appointees, some of whom are major donors in almost every administration — and some of whom set off scandals just as reliably.

A 1983 study by the American Foreign Service Association found that Presidents John F. Kennedy, a Democrat, and Ronald Reagan, a Republican, had tied for the record for political appointees — at 32 percent. And Kennedy’s father, one of the wealthiest Americans of his generation and a major donor to Democrats, with no training as a diplomat, was himself appointed ambassador to England in the run-up to World War II — but left the post in embarrassment after making an undiplomatic comment (“Democracy is finished in England”).

The subject of undiplomatic comments brings us back to Vincent de Roulet, who eventually tired of visa complaints and longed for a more exciting post in Europe. In 1971, he met with Herbert Kalmbach, President Nixon’s personal lawyer, who solicited a $100,000 donation for the upcoming reelection campaign in exchange for a more prestigious ambassadorial post.

But in 1973, at a Senate foreign relations subcommittee hearing on multinational corporations, de Roulet shocked the senators, and his State Department superiors, by describing how he had wielded an implicit threat of interference in the previous year’s election of the Jamaican prime minister. He bragged about a deal he said he made with populist challenger Michael Manley, who had soundly beaten the incumbent: de Roulet promised that the United States would not intervene in the elections and Manley, he claimed, agreed not to propose nationalization of the U.S.-owned bauxite industry. (Bauxite nationalization had never been an issue in the campaign, and Manley denied making any such agreement.)

De Roulet’s testimony prompted Manley to have the ambassador expelled from the country; to further prove Jamaica’s independence from the United States, he also later tripled the taxes and royalties paid on bauxite by American aluminum companies. Not surprisingly, de Roulet didn’t get the coveted European posting, although Kalmbach did offer to refund his campaign contribution. (De Roulet declined.)

“There’s a terrible misconception out there about money in politics, especially with ambassadors,” says Melvin Sembler, the veteran GOP fundraiser whom President George H.W. Bush appointed ambassador to Australia and the Micronesian island nation of Nauru and whom President George W. Bush appointed ambassador to Italy. “You cannot run a campaign without money. Without financing, you have no voice. Why does the president select people who helped him get elected? Because they helped him get elected.”

Lawrence F. O’Brien Jr., director of John F. Kennedy’s successful presidential campaign, as a White House aide had a large role in awarding patronage appointments and then was appointed postmaster general under President Lyndon B. Johnson. He was a little less direct than Sembler in an oral history interview for the archives of the Lyndon B. Johnson Library.

“What you tried to do was to achieve a degree of balance between career appointees and non-career appointees,” he said. “If you had a fellow who had played a significant role in your campaign, he probably had a résumé that would reflect a considerable degree of success in the private sector. Secondly, the fellow was expressing keen interest in being recognized, perhaps a direct request to be considered for an ambassadorship. Yes, the answer is that there were a number of political appointments to ambassadorships, reflecting the president’s appreciation for efforts expended on his behalf.” Such efforts, he said, could mean a large donation.

Nixon was blunter. In June 1971, he told White House Chief of Staff H.R. Haldeman, “My point is that anybody who wants to be an ambassador must at least give $250,000. . . . The contributors have got to be, I mean, a big thing, and I’m not gonna do it for political friends and all that crap.” But, despite Nixon’s determination, the price was apparently still negotiable.

That October, upon learning that New York socialite (and, incidentally, cousin to Ambassador de Roulet’s wife) C.V. “Sonny” Whitney would be nominated as ambassador to Spain, Nixon exclaimed: “Hell, if we did it, it was a great sale. He gave a quarter of a million dollars.” Nixon later withdrew the nomination for fear that Whitney couldn’t get confirmed by a Senate that was considering campaign-finance reform. As Haldeman noted: “He’d have to reveal his financial support. He’d have to lie or reveal it. And that would be a mess, too.” Nixon told Haldeman to give Whitney a refund.

Kalmbach also hit up J. Fife Symington, then the ambassador to Trinidad and Tobago, for $100,000 in a bid for a promotion to Europe, but the administration didn’t approve the transfer. Kalmbach later told the House Judiciary Committee that he also requested $250,000 from Ruth Farkas, a New York philanthropist whose parents had been in real estate and whose husband founded a chain of department stores, in exchange for her appointment as ambassador to Costa Rica. Kalmbach told the committee that Farkas thought a quarter-million dollars was “an awful lot of money for Costa Rica.” Nixon later appointed Farkas ambassador to Luxembourg after she ponied up $300,000 to the ’72 campaign.

For his role in selling ambassadorships to Symington, Kalmbach went to prison. But the Nixon administration’s practice of trading foreign postings for campaign cash didn’t disappear — the campaign reform laws simply drive it underground. Simply writing a check doesn’t work any more. “That went out with Nixon, with campaign finance reform,” says Sembler. These days, the rich and connected are expected to raise money for the candidate from their well-to-do friends.

The practice of sending inexperienced friends and political supporters abroad is nothing new. President Andrew Jackson’s spoils system in the 1830s included ambassador posts for top partisan allies. The 20th century saw the development of a professional diplomatic corps at the State Department, and in the modern era most American ambassadors have been career Foreign Service officers rather than political appointees. But after World War II, as more countries declared independence, the percentage of political appointees increased along with the growing number of U.S. ambassadors. The ratios have varied, but about 30 percent of all ambassadors have been political appointees, ranging from a low of 24 percent during the Jimmy Carter years to the Kennedy-Reagan tie for the record high of 32 percent.

While naming political supporters as ambassadors may be good for presidential fundraising, it’s not always great for diplomacy. That’s in part because political appointees to plum posts overseas tend to fall into three categories: wealthy businessmen, “hostesses” (usually wives or widows of said businessmen), and out-of-work politicians. Many such appointees lack both government service and knowledge of foreign affairs. In 1949, for instance, Harry Truman chose Perle Mesta to be ambassador to Luxembourg. Mesta’s credentials: She was a wealthy widow and Democratic fundraiser known for the lavish Washington parties she threw. Her service as ambassador inspired the 1950 Irving Berlin Broadway musical Call Me Madam, starring Ethel Merman (albeit that the producers maintained, with tongue in cheek, that “neither the character of [the ambassador] Mrs. Sally Adams nor Miss Ethel Merman resemble any person living or dead.”)

Not all political appointees are created equal — or unequal — to the task. Plenty have been stellar ambassadors, among them Mike Mansfield, who served 34 distinguished years in Congress as a Democrat from Montana — almost half that time as Senate majority leader — before President Carter appointed him as ambassador to Japan and President Reagan kept him in the post. And Shirley Temple Black, the Republican former child movie star who served as ambassador to Ghana and later Czechoslovakia, is also regarded as having been a fine diplomat, despite her thin résumé. Evan John Naland, president of the Foreign Service Assocation, whose organization represents career foreign service professionals, says many political appointees have done a good job.

That said, others have confessed wholesale ignorance during interviews and confirmation hearings about the countries or regions to which they’d been appointed. In 1957, President Dwight Eisenhower tapped Maxwell Gluck, the wealthy founder of Darling Shops, a huge chain of women’s clothing stores, to serve in Sri Lanka (then Ceylon). At his confirmation hearing, in closed session, Gluck candidly admitted he could not pronounce the prime minister’s name; of the country’s people, he said, “I think they are a people who are friendly and unfriendly.”

Nominees who fall into the “hostess” category stand out as particularly egregious affronts to the 1980 Foreign Service Act, which decrees that candidates for ambassadorships should possess knowledge of the language of the host country, as well as an understanding of its economic and political institutions and culture, history, and people. For instance, in 1989 the elder President Bush nominated real-estate heiress Joy Silverman as ambassador to Barbados and the Eastern Caribbean. Silverman lacked a college degree, although her résumé did note at least one professional credential: “assisted husband in connection with growth by planning and hosting corporate functions.” But if Silverman was without diplomatic and workplace experience, she nevertheless had what it takes: She and her husband had donated more than $100,000 to the Republican Party. The Senate did not confirm her.

Barbados seems to be a choice spot for professional hostesses: In 2006, the second President Bush nominated the wife of a Washington, D.C.,-area automobile dealer for the same job. Ambassador Mary Ourisman is a Washington board-sitter (the Kennedy Center and the Washington National Opera, among others) known for hosting charity galas and serving on the board and the “decorating committee” of Blair House, the president’s guest quarters for foreign heads of state; along with her husband, the Texas-born socialite is also known in Republican circles for having donated nearly half a million dollars to GOP candidates and causes since 1999. The State Department refused to allow Ambassador Ourisman to be interviewed for this article, instead offering to find a “more appropriate” candidate.

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