Among the many questions to emerge from Ambassador Gordon Sondland’s dramatic and at times farcical testimony during Congress’s impeachment hearings is one so glaring that it’s almost hard to see: How did Sondland, a moderately successful hotelier in Portland, become the U.S. ambassador to the European Union in the first place?

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Sondland, who had formerly been opposed to Trump’s nomination, waged an aggressive lobbying campaign to get into then-President-Elect Trump’s good graces—and paid $1 million for tickets to Trump inaugural celebrations. (The inaugural committee was subpoenaed by federal prosecutors in New York earlier this year.) Rep. Eric Swalwell, a California Democrat, asked Sondland about the donation. “That’s a lot of money, isn’t it?” Sondland grinned and replied: “That’s a lot of money.” That’s also, of course, business as usual in Washington. Most critical ambassadorships typically go to seasoned foreign service veterans, but it’s customary for presidents to hand out many positions—about a third—to top donors and bundlers. The tradition is unique among developed countries and is technically illegal—money isn’t supposed to be a factor in political appointments—but it’s on the rise. Roughly 30% of President Barack Obama’s foreign service appointments were people with political ties—typically donors, according to a paper by Ryan Scoville, an associate professor at Marquette University Law School. Under Trump, that ratio has increased to over 40%, the highest number since Franklin Roosevelt. That shift has been accompanied by a dramatic flight of career foreign service people. ﻿ Scoville has also identified another troubling trend: in recent decades, he writes, “the credentials of the average political appointee have diminished just as the average size of campaign contributions has grown.” For some of Trump’s picks, questions about credentials have raised concerns in Congress and lengthened an already sluggish confirmation process. In a letter last year, Senator Bob Menendez, the top-ranking Democrat on the Senate Foreign Relations Committee, gently reminded Secretary of State Mike Pompeo that all nominees must be properly vetted prior to being nominated. Some nominees, Menendez noted, had not accurately disclosed “the groups, boards, and corporate entities of which they have been a part as well as their financial contributions to political campaigns”; others “failed to disclose lawsuits against them . . . offered misleading answers to questions about knowledge of contacts with Russian officials, or made insulting and inaccurate claims about the country to which they have been nominated to serve as Ambassador.” There were also nominees the committee had seen who “have demonstrated problems of temperament and judgement that should disqualify them for any position representing the United States,” wrote Menendez (who himself is no stranger to charges of corruption). For example, Menendez cited Richard Grenell, a former U.S. spokesperson at the U.N. and Trump’s controversial Ambassador to Germany, whose “undiplomatic and offensive comments have . . . damaged our relationship with a key ally.”

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The trashing of the State Department began with a lackadaisical approach by the Trump White House. After summarily dismissing every political appointee who had served under Obama, Trump took longer than any previous president to appoint senior State Department officials and new ambassadors. For two years, the US had no ambassador in Turkey. Until September’s swearing-in of Lana Marks, a luxury handbag designer and member of Trump’s Mar-a-Lago club, the US went three years without an ambassador in South Africa. The State Department did not return requests for comment from Fast Company, but an agency spokesperson told NBC News earlier this year: “Our Ambassadors are proud to represent the United States of America to some of our most important partners across the globe as they carry out the goals of the Trump Administration,” adding, “These ambassadors’ financial contributions have long been a matter of public record. They are honored the President bestowed this trust upon them, and they hold their service in the highest regard.” Corruption breeds dysfunction but also more corruption. Earlier this month, CBS uncovered evidence that another of Trump’s appointees was involved in an apparent pay-to-play effort: “Papa” Doug Manchester, a San Diego developer and Trump inaugural donor who had been nominated as Ambassador to the Bahamas, hoped to speed up his approval process in the Senate with a $100,000 donation to the Republican National Committee. Manchester withdrew his nomination last week, and the RNC returned the funds. Documents leaked in January 2020 indicate that the marketing firm Cambridge Analytica entered into a contract with Kenneth Braithwaite in 2016, a week before Trump’s election, and a year before Trump nominated Braithwaite to be U.S. Ambassador to Norway. A former business executive and retired rear admiral of the Navy Reserve, Braithwaite left out any mention of the company in his required government disclosure form. Additionally, Braithwaite appeared to have a conflict of interest when he presented a newly-created US Ambassador’s Award to shipping magnate Thomas Wilhelmsen, who runs Norway’s largest shipping company, and whose cousin is married to former Cambridge Analytica CEO Alexander Nix. Braithwaite—whom President Trump has named as his nominee for Secretary of the Navy—has insisted that he had no relationship with the company that would have required disclosure, and told CBS News that he was unaware of the connection to Nix. Trump’s is not the first administration to contain controversial political appointees—two of Obama’s donor-ambassadors turned out to be particularly dysfunctional—and not all donor-ambassadors make for bad diplomats; sometimes their well-heeled connections can be a diplomatic asset. But Trump’s EU Ambassador is one glaring example of what can go wrong. As Sondland tried to outflank career US officials responsible for Ukraine policy—despite the country not being an EU member to begin with—the State Dept’s Fiona Hill told him earlier this year, “Gordon, I think this is all going to blow up.” And so it has, making it clear that moneyed ambassadors can also take American foreign policy in strange, dangerous directions.

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Here are some other top donor-ambassadors in TrumpWorld whose qualifications, biographies, and connections illustrate the new (ab)normal. Joe Cella, ambassador to Fiji, an archipelago of more than 300 islands northeast of New Zealand, as well as the republics of Kiribati and Nauru, and the kingdom of Tonga and Tuvalu, founded the National Catholic Prayer Breakfast in 2004. He also cofounded the Catholic political action committee Catholic Vote, also known as Fidelis, and since 2010 has served as principal of a Catholic consulting firm the Pontifex Group. While he once signed a letter declaring Trump “manifestly unfit to be president of the United States,” Cella led the Trump campaign’s Catholic advisory council during the 2016 election. David B. Cornstein, ambassador to Hungary, is a businessman and frequent GOP donor who has much in common with his friend Donald Trump: As AllGov reported last year, they are “both New Yorkers who have winter homes in Palm Beach, they’re both very rich and they’ve both led money-losing gambling operations.” A former member of Trump’s Florida golf club, Cornstein served as chairman of New York City’s Off-Track Betting Corporation before its financial demise. In recent years, he was chairman of Circa, a company that buys high-end used jewelry, and president of Pinnacle Advisors Limited, a private wealth management company. Ambassador David B. Cornstein was honored to meet with Speaker of the National Assembly László Kövér today. During a tour of the Parliament building, Ambassador Cornstein was also able to admire the Holy Crown and the Coronation Insignia. ????????️????????️ #USAmbHungary pic.twitter.com/9gxMhOGHZh — US Embassy Budapest (@usembbudapest) June 27, 2018 His ambassadorship has been overshadowed by questions about his vocal support for the right-wing government of Hungarian President Viktor Orban, in contradiction of State Department policy. At a lavish Independence Day bash at the embassy in Budapest this summer, Paul Anka—flown in by the ambassador for the occasion—serenaded Orban with a personalized rendition of “My Way,” reported the New York Times .

. In 1999, he was named chairman of TeleHubLink, a telemarketing company that produced wireless encryption products. In 2001, TeleHubLink was sued by New York’s top prosecutor for scamming consumers across the country. “Using the name Triple Gold Benefits,” New York State Attorney General Eliot Spitzer argued in 2001, Cornstein’s company had “promised thousands of consumers across the nation that, for an advance fee of over $200, the consumers would receive a low rate, general purpose Visa or MasterCard credit card. In fact, consumers who paid the advance fee did not receive a credit card. Instead, Telehublink sent them a ‘discount benefits package’ consisting of generally worthless items such as an application for a credit card.”

A 2001 decision by a State Supreme Court awarded restitution to victimized consumers, and, after an appeal by the company, a 2003 judgement reaffirmed the original ruling. That didn’t diminish Cornstein’s political capital: in 2001, shortly after being appointed to the board of the Battery Park City Authority, New York’s then-governor George Pataki gave Cornstein the chairmanship of the New York State Olympic Games Commission as it prepared a bid for the 2012 games. (London eventually won.)

Telehublink appeared to have profited handsomely during that time. According to documents filed with the Securities and Exchange Commission, Cornstein’s company reported a surge in revenues, from $1 million in 1999 to over $9.2 million in 2000, in large part due to Triple Gold Benefits sales. Cornstein later donated to former nemesis Spitzer’s successful campaign for governor. Kelly Craft, ambassador to the United Nations, along with her husband, Joseph Craft III, contributed at least $1 million to Trump’s inaugural celebrations. (The inaugural committee was subpoenaed by federal prosecutors in New York earlier this year as part of a probe into possible campaign finance violations.) The Crafts also have “gold”-level status at Trump hotels, which designates customers who have stayed more than 20 times, a number the Washington Post said was “unusually high.” She’s also donated to more than half of the Repubican senators on the Foreign Relations Committee that was charged with approving her nomination. Joseph is the longtime CEO of coal giant Alliance Resource Partners, which critics say presents a conflict of interest when it comes to his wife’s role in international discussions on climate and the environment. As a mother, it touches my heart to see parents so desperate for their children to have a future and an education. They have fled #Maduro and their homes in Venezuela. I encourage them to keep being a voice against this oppressive regime. I will be an even stronger voice as well. pic.twitter.com/bMa6uIIqzb — Ambassador Kelly Craft (@USAmbUN) November 19, 2019

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And Democratic Sen. Elizabeth Warren has pledged to end the practice if elected. “This is Washington corruption at its worst,” she said at the last debate. “I’ve pledged never to give ambassadorial positions to wealthy donors—and every candidate should do the same.” So far, no other candidate has joined her. This story has been updated.