Bush was the latest to disappoint. Sondland “kept talking about it,” said a fellow Bush donor, adding that “2016 was not turning out remotely as we had expected.”

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To realize his goal, Sondland made a political about-face and backed Donald Trump, a candidate he once said was out of touch with his “personal beliefs and values on so many levels.” After the election, Sondland contributed $1 million to Trump’s inaugural committee. And he began calling in political favors — including from Republican National Committee chairman turned White House Chief of Staff Reince Priebus — to convince Trump that he could be a team player.

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Now, the lengths to which Sondland would go to impress Trump — and to advance the president’s agenda in Ukraine as U.S. ambassador to the European Union — have made him a central figure in the congressional impeachment inquiry. Sondland is scheduled to testify under subpoena this week before House investigators.

Of particular interest is Sondland’s work over the summer with U.S. diplomats in Kiev and Trump’s personal lawyer Rudolph W. Giuliani. Together, they pressed Ukrainian leaders to issue a public statement committing to investigating corruption at a Ukrainian energy company. The move would have tarnished the character of Trump’s potential 2020 rival, former vice president Joe Biden, whose son served on the company’s board. The Washington Post reported Saturday that Sondland plans to testify that he understood that, in exchange for the statement, Ukrainian President Volodymyr Zelensky would receive a coveted invitation to visit the White House.

Current and former U.S. officials and foreign diplomats say Sondland seemed to believe that if he delivered for Trump in Ukraine, he could ascend in the ranks of government. A person close to Sondland disputed that notion, but other officials said Sondland had been talked about in the administration as a possible successor to Commerce Secretary Wilbur Ross.

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“He spent a year trying to prove that he wasn’t anti-Trump,” said a former White House official who watched Sondland’s role evolve. “He got into the position [of ambassador], and he had an opportunity to prove it. Trump knew that he wanted to prove his loyalty.”

This story is based on more than three dozen interviews with diplomats in the United States and abroad, current and former government officials, and associates and confidants of Sondland. Many spoke on the condition of anonymity because they feared retaliation or were discussing sensitive diplomatic topics.

Sondland, 62, declined through an attorney to comment. But his wife, Katherine Durant, criticized coverage of her husband, saying in an interview that only those motivated by self-interest were speaking. Durant has mostly remained in Portland during Sondland’s posting abroad, she said, helping to run the hotel business he founded. She said she fears an economic backlash against the hotel company. Already a prominent local company has cut ties with Provenance Hotels, and a Democratic congressman, Earl Blumenauer, has called for a boycott until Sondland cooperates fully in the impeachment inquiry.

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“We live in a world right now where there’s no upside to supporting someone like Gordon who is working for Trump; it’s a mob,” Durant said.

She said her husband deserves a fair hearing: “He’s been extremely hard-working. He came from immigrant parents; he’s first generation here; he made his own wealth; he’s worked his entire life hard, he’s extremely generous. I mean, he’ll sit down and listen to anyone, take his time, go to bat for them, give his money. But this environment is so sad and vicious that there is no one who will stick up for him. I find it really pathetic.”

A collector of relationships

In March 2016, shortly after the phone call from Bush, which was described by two people with knowledge of it, Sondland was the headliner at the Portland Business Journal’s monthly Power Breakfast.

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More than 400 business leaders gathered in a ballroom at 7 a.m. Sondland took the microphone and began recounting his rags-to-riches tale.

In Sondland’s telling, the story begins with his teenage parents fleeing Nazi Germany. His mother makes her way to Uruguay, while his father ends up fighting with the French Foreign Legion in North Africa. The two stay in touch through letters delivered by the Red Cross. They reunite after six years and make their way to Seattle, where they run a dry-cleaning business. Sondland is raised on Mercer Island, now an exclusive area east of downtown but one that in the 1960s and 1970s was more of a melting pot.

“Everyone mixed in the same high school,” he recalled, “so that created a lot of aspirational emotions when you saw some kids showing up on their 16th birthday with the new BMW that their parents had bought them, and some kids had to walk or take the bus.

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“It created a lot of interesting dynamics that probably followed me for the rest of my life.”

Sondland found success in business at an early age. At 28, as a commercial real estate broker, he was analyzing whether his firm should become the listing agent for a hotel in bankruptcy. Reviewing the company’s financials, he saw an opportunity. He decided to look for investors and buy it himself instead. It was the start of what would become Provenance Hotels, a boutique chain with more than a dozen properties throughout the country.

As the company grew, Sondland and Durant became known as major philanthropists in Portland. They donated millions of dollars to medical research, homeless programs and the arts, including endowing in perpetuity free admission to the Portland Art Museum for anyone under 18.

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But increasingly, his wife said, Sondland’s obsession was politics. “I don’t know what you’re into, but his sports, his golf, it’s all politics,” Durant said. “He loves it.”

A lifelong Republican, Sondland became a “bundler” — a political fundraiser who collects contributions from other donors and then directs large, six-to-seven-figure donations to campaigns. He backed Mitt Romney and John McCain that way.

Sondland also has donated smaller sums to Democrats, particularly at the state level. Widening his network of wealthy donors seemed almost like a hobby for Sondland, said David Nierenberg, an investment adviser in Washington state who has known Sondland for more than a decade.

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“Some people collect cars. Some people collect wine, collect books. Gordon collects relationships — and relationships with people who are active in public life are very important to him,” Nierenberg said.

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While the two men were raising money for Romney, Sondland told Nierenberg that he had expressed interest in a potential ambassadorship. He hoped to follow the path of two previous political fundraisers from the area who had been rewarded with ambassadorships by President George W. Bush: Charles “Butch” Swindells and Bill McCormick, of the seafood restaurant chain McCormick & Schmick’s.

“Gordon indicated to me . . . that it would be of interest to him to go to a German-speaking country, like Germany or Austria, since it would be a full circle” for him as a child of Holocaust survivors, Nierenberg said.

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Sondland’s hoped-for path was also clear to Oregon developer Jordan Schnitzer, a Democratic donor and a longtime friend. Sondland became “very enamored” with the jet-setting lives of McCormick and Swindells, Schnitzer said.

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“Gordon was very close to those people, and I think he admired the fact that they were ambassadors,” Schnitzer said. “So for a number of years, it’s been clear for many of us he wanted to become an ambassador, therefore he became very generous with his political contributions.”

'Always a quid pro quo'

As a Republican in the majority-Democrat Pacific Northwest, Sondland developed an understanding of what he considered the transactional nature of bipartisan politics.

In the early 2000s, his financial support to the campaigns of George W. Bush helped put him on the radar for a modest appointment to the President’s Commission on White House Fellowships. At the same time, his support for the Democratic governor of Oregon, Ted Kulongoski, led to an appointment as head of the Governor’s Office of Film & Television.

“The governor knew I had a relationship with the Bush White House and asked me to work on myriad projects,” Sondland told the Portland Business Journal’s breakfast audience. “As things came up . . . we would make these requests and they were done quietly. They were done with rifle precision and there was always a quid pro quo: The governor would help the president with something, and the president would help the governor with something. And it was very transactional.”

At the time of the breakfast, Sondland had not yet gone all in on Trump — a reversal that was in its own way transactional and that followed a path many other establishment Republicans also have taken.

In August 2016, Sondland and his business partner, Bashar Wali, took their names off a scheduled Trump fundraiser, after the candidate belittled the parents of Humayun Khan, a Muslim soldier slain in Iraq while serving in the U.S. Army.

Their company issued a public statement noting Sondland’s parents’ flight from Germany and Wali’s emigration from Syria. “In light of Mr. Trump’s treatment of the Khan family and the fact his constantly evolving positions diverge from their personal beliefs and values on so many levels, neither Mr. Sondland or Mr. Wali can support his candidacy,” the statement concluded.

Rob Freres, the president of an Oregon timber company who had been on the receiving end of Sondland’s fundraising pitches, wondered whether Sondland was trying to protect his business empire, especially since a Trump victory still seemed unlikely.

“I thought that [because of] where he is in the hotel business, it was just prudent for him to back away because of the threats or bodily harm, or vandalism of his properties,” Freres said.

Sondland’s approach changed after Election Day. While he still didn’t publicly support Trump in Portland, where opposition to the incoming president was already prompting street protests, Sondland donated $1 million to Trump’s inaugural committee through four entities, including limited liability companies, state and federal records show. The contributions made him one of the top 50 donors to a record-setting inaugural haul of $107 million.

When the donations were reported in 2017, “everyone in Portland was pretty bummed,” said a business associate of Sondland’s. “Gordon was cutthroat, no doubt, but he had done so many good things for Portland, this seemed like a betrayal.”

Those who knew his ambition for becoming an ambassador were less surprised.

“Knowing of Gordon’s interest in having relationships with people in power, and knowing that he was sort of ecumenical about that — between Democrats and Republicans — no, I was not surprised,” Nierenberg said.

Sondland’s work to ingratiate himself with Trump was just beginning.

He asked Priebus to recommend that he be appointed ambassador to the European Union, according to people knowledgeable about the exchange.

Initially, Trump balked.

“He had a hard time winning Trump’s approval because he left Trump during the campaign,” said a former White House official familiar with the president’s reaction.

Sondland called on Trump’s former campaign finance chairman, Treasury Secretary Steven Mnuchin, who had invited former Bush donors to back Trump, to put in a good word, according to current and former White House officials. Sondland also sought the backing of Jared Kushner and Ivanka Trump, arranging a private dinner with them, officials said.

To some in Trump’s inner circle, Sondland’s ambition seemed transparent.

“He was clamoring to be an ambassador. He gave a ton of money. He worked year after year,” one official said. “He likes to go to events, to be seen, to feel like he’s in the room.”

Eventually, Trump decided Sondland was on his team. He announced the nomination on May 10, 2018.

A 'disruptive diplomat'

The role of U.S. ambassador to the European Union has long been considered one of the most “nerdy” jobs in the State Department, according to past officeholders. People with previous government experience or skilled lawyers from the private sector have been tapped for the technocratic job of finding ways to build coalitions to advance American interests.

Culturally, past ambassadors have taken care to learn the lingo of Brussels, where it is assumed diplomats will understand that “comitology” refers to how the E.U. modifies its laws and that the “European Semester” is when E.U. countries coordinate their budgets with the bloc. Significantly, the ambassador’s portfolio typically has included Europe-wide energy issues, including gas supplies that run in pipelines through Ukraine.

Sondland came in with boisterous self-confidence and a conspicuous style. From the day he arrived in Brussels, the office’s official Twitter account chronicled his every handshake and salute. He posted a YouTube video of him and his family at home, making coffee and sitting on a couch introducing himself to his European audience.

In public appearances and in private meetings, Sondland often came off like a version of Trump with the roughest edges sanded off, according to diplomats who interacted with him. He once declared to American business representatives that unlike his predecessors he would “get s--- done,” according to people who were present. He called the European Union “out of touch” and accused it of stalling on trade talks with the Trump administration. And he called himself a “disruptive diplomat.”

From the outset, Sondland’s ambition was clear, as was his fondness for the trappings of the job, said several who interacted with him.

He began updating the U.S. ambassador’s baronial residence on the leafy outskirts of Brussels, an effort that was still underway last week, according to a guard who said the residence was closed for extensive renovations. Contracts went out for tens of thousands of dollars in new furniture, $25,000 to an American rug company, and as much for the services of a custom woodwork and case maker, federal procurement records show.

It was “real 18th century Jefferson-in-Paris behavior,” a senior U.S. official said.

A person who has spoken to Sondland about the upgrades said the residence was “nearly unusable for representational purposes,” and renovations were a less-costly alternative to a planned purchase of a new mission facility, initially proposed during the Obama administration.

Early on, Sondland tried to invite the European Union’s top officials — heads of state — to dine at the residence. The request raised eyebrows on the European side, officials said at the time, because ambassadors, even American ones, usually aim lower in the pecking order as a matter of protocol.

At dinners and elsewhere, Sondland was aggressive in echoing Trump’s rhetoric, telling people that Europe had been taking advantage of the United States on trade for decades and sometimes punctuating his speech with four-letter words.

In June, at a dinner with U.S. and European officials, Sondland was seated across a table from Baroness Catherine Ashton, a former E.U. foreign policy chief.

According to two people who observed the encounter, he spoke at length about American generosity after World War II and how it paved the way for the continent’s current prosperity. He asked why Europeans were not more appreciative, the observers said, and why his requests were so frequently rebuffed.

Ashton politely told him that the United States had also benefited from Europe’s prosperity, said two American guests who observed the exchange. She did not return calls seeking comment.

A few months into his posting, Sondland and Schnitzer were vacationing at their beach homes in Gearhart, Ore., Schnitzer said. Sondland spoke about the challenges of navigating governmental bureaucracies and bemoaned what he saw as inefficiency, Schnitzer said.

But Sondland added that he “got to meet all these European leaders and he was often on first-name basis with them, even though you’re supposed to address them as ‘president this or president that.’ He said, ‘I could address them by their first name,’ ” Schnitzer said. “I took it as he was building a number of impressive relationships.”

A special assignment

In recent months, Sondland’s deep involvement in a new administration in Ukraine struck diplomats in Brussels and Washington as highly unusual, given his role as envoy to the European Union, a large political bloc that does not include Ukraine.

In July, on a visit to the former Soviet republic, Sondland told a Ukrainian broadcaster that Trump “has not only honored me with the job of being the U.S. ambassador to the E.U. but he’s also given me other special assignments including Ukraine.”

But Sondland plans to tell Congress this week that the roots of the confounding task of securing a pledge from Zelensky began in May, according to a person familiar with the testimony. Sondland attended Zelensky’s inauguration that month.

In an Oval Office meeting afterward, Sondland intends to say, Trump told him, special U.S. envoy to Ukraine Kurt Volker and Energy Secretary Rick Perry that any face-to-face meeting he would entertain with the new Ukrainian president would have to be cleared by Giuliani, the president’s personal attorney.

Sondland plans to say that over the following weeks, he and Volker, along with the acting ambassador to Ukraine, William B. Taylor, learned that as a condition of such a meeting, Giuliani was demanding that Zelensky’s administration publicly announce it would tackle corruption, including singling out as a target Burisma, the Ukrainian energy company linked to Biden’s son.

Text messages that Volker has turned over to Congress show the three struggling to negotiate the details of that statement with Ukrainian officials.

Volker writes most often. Taylor frequently expresses concern. Sondland on at least one occasion appeared to speak for Trump’s interests, writing on Aug. 9 that “potus really wants the deliverable.”

Volker did not respond to messages seeking comment for this story. Taylor declined to comment.

Giuliani last week told The Post that Sondland “seemed to be in charge” of the overall effort. He said that Volker first raised the idea of getting the Ukrainians to issue a statement, and that Volker and Sondland were involved in the specifics of getting Ukraine to name Burisma.

“I said it should include collusion and Burisma,” Giuliani said. “It’s quite possible we never mentioned Biden. Of course, Biden was part of that.”

Giuliani said that Sondland and Volker were often on conference calls together and that Sondland was keeping tabs on Giuliani’s work on the effort, speaking with him about six times over the summer.

But according to the person with knowledge of Sondland’s testimony, Giuliani had the more central role. Volker, Taylor and Sondland were all just trying to “understand through Rudy what the president’s concerns were and to try to address them,” the person said.

Sondland plans to say he was unaware until a whistleblower’s complaint became public late last month that Biden’s son Hunter had been a Burisma board member and that some government officials suspected Trump’s goal was to tarnish the character of a potential 2020 Democratic challenger. In their discussions, Giuliani never mentioned the Biden connection, the person with knowledge of Sondland’s testimony said.

Sondland could face skeptical questioning on this point. In televised appearances, Giuliani had by then repeatedly raised concerns over Hunter Biden’s role at Burisma, and numerous newspaper and magazine articles had questioned whether the issue could prove to be a drag on his father’s presidential campaign.

He is also likely to be pressed on his own interactions with Trump. The person close to Sondland said the ambassador spoke to Trump maybe “six or seven” times as ambassador, including three times in the course of the Ukraine negotiations, though not about the statement sought by the administration.

Last month, after speaking with the president by phone, Sondland sent a key text message. It said that Trump wants “no quid pro quo’s of any kind.” Trump and his supporters have held up the text as proof that none was ever considered.

The person with knowledge of Sondland’s testimony said that Sondland took Trump at his word at the time but that he has no knowledge of whether the president’s statement was true, as he only learned details such as the importance of the Biden mention from the whistleblower’s complaint.

Nierenberg, Sondland’s acquaintance from Portland, said he sent him an email recently urging that in the impeachment inquiry Sondland “tell the truth, the whole truth, and nothing but the truth.”

Nierenberg said Sondland wrote back thanking him for the advice.