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How Gordon Sondland, ‘a Guided Missile for Getting Access,’ Landed in the Middle of Trump’s Ukrainian Mess

In 2003, as George W. Bush’s White House echoed with talk of an “axis of evil,” Gordon Sondland, the man who is now President Donald Trump’s top diplomatic emissary to the European Union, was bird-hunting in rural Oregon with Ted Kulongoski, the state’s then-governor, the latter’s bodyguards trailing.

Turning to the life-long Democrat, Sondland gestured at the bodyguards’ holstered pistols, and said, “I hope those nine-millimeters have bullets in them,” recalls Jamsheed “Jim” Ameri, an Iranian-born Oregon businessman who in that moment was standing next to Kulongoski.

“Why?” asked Kulongoski.

“Well,” replied Sondland, “You’ve got this Iranian with a shotgun to your right.”

Kulongoski was tongue-tied.

But Ameri recalls erupting in laughter at the joke. In addition to being smart, Ameri says, his friend, the current U.S. ambassador, is “crazy-funny” and “always laughing.” Though maybe not so much these days.

That’s because Sondland’s role in the Trump administration’s campaign to pressure Ukraine is now being analyzed under a national microscope. After resisting a summons from Congress to testify last week, Sondland was subpoenaed in the impeachment inquiry, and has agreed to testify before multiple congressional committees Thursday morning.

Gordon Sondland, U.S. ambassador to the European Union, arrives at the Capitol for his deposition as part of the House’s impeachment inquiry on Thursday, Oct. 17, 2019.
Photo By Bill Clark/CQ-Roll Call, Inc via Getty Images

In advance of his hearing, the ambassador released his opening statement, prepared remarks that were obtained by Fortune that say the president directed State Department emissaries to work with Rudy Giuliani, Trump’s personal attorney, on Ukrainian matters. Sondland’s statement also says Giuliani discussed the 2016 election, a missing Democratic National Committee email server purportedly containing missing Hillary Clinton emails, and Burisma (the company that Joe Biden’s son Hunter served on the board of) as Ukrainian anti-corruption investigatory topics of importance to the president.

Sondland’s testimony with the House Oversight, Intelligence, and Foreign Affairs Committees is scheduled to begin at 9:30 a.m., and the diplomat says he plans on answering the committee’s questions “fully and truthfully.”

A divining rod for people with power

Ameri’s bird-hunting anecdote reflects what Sondland’s defenders and critics agree is a sometimes blunt man with no shortage of ego. Employing brains, activism, and political contributions, Sondland has worked for decades to ingratiate himself with political, business, and entertainment elite—whether it be a Republican fundraiser with Jay Leno, or a dinner with Portlandia star Carrie Brownstein and Democratic Oregon governor John Kitzhaber. Trump’s E.U. ambassadorship is undoubtedly Sondland’s crowning transactional achievement.

And Ameri himself was not just any businessman. His then-wife was a budding Congressional candidate who under President George W. Bush, became an Assistant Secretary of State, then head of the U.S. delegation to the United Nations. Sondland, who reportedly has long harbored ambassadorial ambitions, joined Ameri in visiting his wife in Geneva.

“He’s a divining rod for people with political power,” an associate of Kulongoski’s says of Sondland, speaking on the condition of anonymity because he was not authorized to comment. “If you walk into a crowded room and you’re looking for the most powerful person, look for Gordon, because you know he’s tall and he’ll be within five feet of them.”

Sondland, according to his wife and business partner Katy Durant, wanted to become an ambassador because he is fixated on politics and loves playing a “behind the scenes” role. Durant echoed others in saying “he loves to do deals” and be in the thick of it. Sondland, through a representative, declined to comment for this story.

It’s in those traits that lie the roots of Sondland’s current plight, say people who know him. Oregon Democrats valued him because he was politically flexible, not ideological, and could be an entree to GOP circles. Sondland and Durant, who’s long been a registered Democrat, gave generously to both parties. And despite a healthy ego, he was considered pretty harmless.

“He was viewed as a somewhat naive player,” says the Kulongoski associate, reflecting on Sondland’s rise. “If you’re kind of naive in Oregon politics, and you think you’re going to be able to navigate Ukrainian and D.C. politics? Unbelievable—that takes some confidence.”

It’s unclear how Sondland, a bundler for Mitt Romney’s 2012 campaign who supported Jeb Bush in 2015, originally connected with Trump. On July 1, 2016, the Republican National Committee and Trump campaign announced Sondland would be state chairman of their joint fundraising. In August 2016, when his role hosting a Trump fundraiser hit local papers, Sondland pulled out, saying he did not approve of Trump’s policies.

After Trump’s election, however, Sondland secretly contributed $1 million to Trump’s inauguration through four companies he controlled. Trump nominated Sondland to be the U.S. ambassador to the E.U. in May 2018. His approval was among the smoothest of Trump’s political appointments, and in June he began life as a U.S. diplomat.

Earlier this week, Durant, dismissed rumors of an earlier financial connection to Trump, claiming the two men had never met previously. Sondland “was at a hotel conference and like, met him in an elevator one time,” she says.

The anti-Trump?

Sondland’s defenders describe him as a self-made man, but he did have help.

His parents, having escaped Germany before the Holocaust, spent most of their savings in 1953 while moving from Uruguay to Seattle. There the Jewish couple opened a dry-cleaning business in a rental space and bought a small house. Sondland was born in 1957, and his sister, who was 18 years his elder, became a second mother to him as their parents worked long hours.

Sondland took classes at the University of Washington, but dropped out and went into commercial real estate sales. In 1985, the 28-year-old Sondland saw a business opportunity in a bankrupt Seattle hotel, the Roosevelt. To raise the reported $7.8 million needed, he tapped friends and family, including his wealthy brother-in-law who went on to collaborate on several deals with Sondland.

In 1991 Sondland met Durant, a Portland real estate broker who was already affluent, and the two joined forces in business and in life, marrying two years later. In January 2018, Oregon Business named the two a “power couple.”

Sondland headed Aspen Capital, a company with services that include hard-money loans, part of a group of investors who pool funds on deals and projects through a web of interlocking limited liability corporations. Aspen boasted of a 48-hour turnaround for projects in need of cash, according to a cached image of its 2006 website: “Need financing? We have it. Hate red tape? We abhor it.”

Screengrab of Aspen Capital’s 2006 website, from the Internet Archive

Durant, meanwhile, manages her own company, Atlas Investments, which shares a downtown Portland headquarters with Provenance Hotels, also known as Aspen Lodging Group, another company Sondland co-founded. Durant took over as the company’s chairman last summer, when Sondland’s ambassadorship began.

Provenance owns and operates 14 hotels, including six in Portland as well as others in Washington state, Boston, Nashville, New Orleans, and Palm Springs. The properties are the opposite of Trump’s gold and garish decor. Understated with a focus on arts and culture, each has a name and identity intended to create a narrative for guests. For instance, Portland’s Hotel Lucia was named after Sondland and Durant’s daughter, and Seattle’s Hotel Max after their son. (Contrary to local rumors in Portland, Sondland’s Hotel Dossier was named prior to the Steele Dossier’s release, though it’s unclear who named its now-defunct restaurant, Omerta.)

Sondland’s federal financial disclosure statement shows he and Durant have interests in dozens of holding companies, real estate firms, and LLCs across several states, with assets of at least $78 million. The couple reported income for 2018 and four months of 2019 amounting to between $5.4 million and $9.3 million.

“He’s renovated these hotels and he’s done a good job and made money,” said Portland developer Robert Ball. “He’s worked really hard.”

Taxes, donations, and deals

In business, Sondland and Durant have largely avoided major controversy, with some exceptions.

In 2005, Kulongoski named Durant to the Oregon Investment Council, overseeing a portfolio of state and local pension funds that topped $60 billion at the time—where she served until 2017. The council often invested in companies Durant and Sondland did business with, causing Oregon investment advisor Bill Parish to describe it as a case study in the need for more S.E.C. oversight.

Durant, for her part, said she recused herself whenever called for, and noted that she led a battle against exorbitant fees charged by equity firms. Durant says she chaired the council as a way of giving back. “I care about my state,” she says, adding that she “probably saved the state hundreds of millions of dollars.”

Scrutiny over Durant’s appointment publicly revealed that Sondland claims residency in Seattle on his tax returns, taking advantage of Washington state’s lack of an income tax. He has done this despite having raised two children in Portland, run businesses there, sat on local nonprofit boards, and registered cars in Oregon. The only state income tax Sondland pays are on wages derived from Oregon firms. Declaring residency in Oregon would mean he would be taxed on his entire income.

Durant defends the arrangement, calling his residency in Seattle “the secret of my successful marriage”—but she concedes he lives in both locations.

Meanwhile, Sondland has given generously to Oregon institutions, establishing himself as a major philanthropic player. He served on the boards of the Portland Art Museum and the Oregon Health & Sciences University, and has given major sums to other nonprofits like the Cascade AIDS Project and a homeless services group, New Avenues for Youth. This year, Provenance was a major sponsor of the Human Rights Campaign, a group specializing in LGBTQ issues. “We know we’ve been super-blessed, and want to give back,” Durant says.

However, a 2010 Oregonian investigation reviewed Aspen’s home mortgage affiliate, Gregory Funding, found about half of its loans ended in foreclosure. In 2012 the state of Oregon fined Gregory $50,000—a large sum for Oregon—for several legal violations around business practices, and there have been several consumer complaints filed with the Oregon Department of Justice by homeowners claiming mistreatment. Gregory settled for $40,000, admitting no wrongdoing, the Oregonian reports.

Sondland’s most prolonged and high-profile Portland scrap, however, saw him fighting plans by a regional planning agency, Metro, to fund a convention center hotel. Arguing for free-market principles for a decade, Sondland ultimately dropped his principled stand and three lawsuits in return for a prime piece of land. But before settling, Sondland reportedly asked Metro to let him take over the project, seemingly dropping his principled stand from before.

Kevin Looper, a top Democratic strategist who has advised the last three Oregon governors, cites this high-profile flip-flop as why Sondland’s viewed in Oregon political circles as “notoriously unencumbered by self-awareness.”

‘No quid pro quo’s of any kind’

Whether Sondland’s self-awareness ultimately kept himself and the administration out of diplomatic trouble may play out behind the closed-doors of Thursday morning’s congressional hearings. The committees will undoubtedly attempt to discern why Trump tapped Sondland, his E.U. envoy, to handle the nation’s Ukraine affairs.

Understanding the Portland hotelier’s personal history and personality may provide insight on why. “He’s a guided missile for getting access to the most powerful person,” says the Kulongoski associate. “He goes around any obstacle, including staff.”

Even before his congressional testimony Thursday morning, Sondland is squarely at the center of the scandal. The controversy began with a whistleblower complaint over a July 25 phone call between President Trump and Ukrainian President Volodymr Zelensky. A resulting impeachment inquiry into Trump has alleged that the administration withheld military assistance from Ukraine to extract what amounts to campaign help. The whistleblower complaint, filed Aug. 12 and released Sept. 26, says Sondland provided Ukrainians with advice on how to “navigate” Trump’s demands.

Meanwhile texts released Oct. 3 show how Sondland pushed to advance Guliani’s agenda to spark a Ukrainian investigation into Democratic presidential front-runner and former Vice President Joe Biden. In the texts, Sondland also pushes back against Ambassador Bill Taylor’s questioning of the arrangement—after a four-and-a-half hour lapse in which it’s been reported that the E.U. ambassador spoke with Trump—writing, “The President has been crystal clear no quid pro quo’s of any kind.”

On Monday, former U.S. Ambassador to the Ukraine, Fiona Hill testified that then national security advisor John Bolton encouraged her to report Ukraine machinations involving Sondland and Trump chief of staff Mick Mulvaney to White House lawyers, providing what, according to multiple media reports, is a quote for the ages: “I am not part of whatever drug deal Sondland and Mulvaney are cooking up.”

Meanwhile, as media outlets continue to dig into the Ukraine mess, some portrayals have suggested Sondland hoped for, or maybe was dangled, a higher post, such as U.S. Commerce Secretary to succeed Wilbur Ross. Sondland’s wife dismisses the idea. “To my knowledge, he was not being looked at for a higher level position,” she says.

Additionally, on Wednesday the Washington Post reported Sondland had spearheaded a $1-million renovation of his official home outside Belgium—news that would not surprise acquaintances in Oregon familiar with his taste for finer things—including a personal art collection worth as much as $25 million, according to his financial disclosure.

Durant says the media attention has been overblown, misleading, and often wrong. “The factual inaccuracies are just mind-boggling right now,” she says, adding that the news has stoked a mob mentality among Trump critics. One article falsely claimed her company scrubbed Sondland from its website in response to the Ukraine controversy, another claimed his birthday was the day before the article. (It actually was in July.) Not only that, she says, but “I’m getting all sorts of threatening emails and phone calls.”

Indeed, Portland, the liberal enclave that it is, has been abuzz with Sondland news, ever since the hotelier’s involvement with Trump was revealed in 2016. Last week, after the Ukraine texts were released, the city’s congressman, Earl Blumenauer (D-Ore.), even called for a boycott of Sondland’s Portland hotels, a move that prompted Provenance Hotels to file an ethics complaint against the 12-term representative.

Blumenauer has since gone quiet, but pro-impeachment marchers on Sunday took to the sidewalks in front of the Heathman, the Sondland’s oldest and most revered Portland hotel. Several hundred protestors circled the Heathman, many sporting handpainted “Impeach Now!” signs. And they all shouted a rhythmic chant in unison: “Gordon Sondland, tell the truth!”

More must-read stories from Fortune:

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—Trump impeachment inquiry: Who has been subpoenaed—and why
5 lessons history has taught us about impeachment
—Most Americans favor an impeachment inquiry—but are wary of removing Trump, polls find
—How the circumstances around Donald Trump’s impeachment inquiry differ from Bill Clinton’s
—How whistleblowers have taken down titans of American business
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