For more than two decades, Pacific Northwest hotelier Gordon Sondland has been a prolific political donor, cultivating ties to successive GOP presidential contenders in part, associates say, to fulfill a dream of landing an ambassadorship.

But in 2016, when then-presidential nominee Donald Trump insulted the parents of a U.S. soldier killed in Iraq, Sondland decided it was a bridge too far. Although he was a state co-chair for the Trump campaign, Sondland repudiated the nominee and backed out of a high-dollar fundraiser scheduled in Seattle.

Then Trump won.

Just a few months after his disavowal, Sondland reversed course and gave Trump’s inaugural committee $1 million, routed through four separate LLCs. A year later Trump rewarded Sondland, who had no prior diplomatic experience, naming him U.S. ambassador to the European Union.

Now Sondland, a Mercer Island native whose refugee parents ran a dry-cleaning business in West Seattle for a quarter-century, is at the center of the House impeachment inquiry of Trump. After building a successful business that gave him vast wealth and prestige as a philanthropist, Sondland, 62, is now embroiled in a scandal that risks defining his career.

He is named in the whistleblower report that led to the impeachment investigation into Trump’s alleged abuse of power, and has been asked to testify before Congress this coming week.

Text messages released by House Democrats on Thursday show Sondland responding to another diplomat who objected to a seeming quid pro quo — linking U.S. foreign policy in Ukraine with Trump’s political interests.

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“As I said on the phone, I think it’s crazy to withhold security assistance for help with a political campaign,” wrote veteran diplomat Bill Taylor on Sept. 9.

Sondland responded hours later, saying Taylor was “incorrect” and that the president had been “crystal clear no quid pro quo’s of any kind.” He added: “I suggest we stop texting back and forth.”

Sondland is not a household name in Seattle, or even in state GOP politics, although he is a major civic and power player in Oregon. But he has long maintained his voter registration in downtown Seattle at Hotel Theodore, part of the Portland-based boutique hotel chain he founded.

“Always a quid pro quo”

Like many establishment Republican donors, Sondland was not originally a Trump supporter. He started out backing former Florida Gov. Jeb Bush, donating $25,000 to his super PAC.

Sondland’s political giving has been overwhelmingly to Republicans, with more than $420,000 going to GOP candidates for federal office since the late 1980s, versus about $25,000 for Democrats.

But he’s maintained friendly ties to prominent Democrats. He was on the transition team of Oregon Gov. Ted Kulongoski, a Democrat, when he took office in 2003, and Kulongoski made him chairman of the Governor’s Office of Film and Television. Sondland also served as a liaison between Kulongoski and George W. Bush’s White House.

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In a 2016 interview Sondland decried rising partisanship and looked back fondly on his days helping a liberal governor ask for aid from a conservative president. But his language — extolling the transactional nature of politics — is striking given the controversy he’s involved in now.

“We would make these requests and they were done quietly, they were done with rifle precision and there was always a quid pro quo,” Sondland said at an event for Portland business leaders in 2016. “The governor would help the president with something and the president would help the governor with something and it was very transactional.”

Now, “there’s less transactional, there’s less comity, there’s less ability to understand what someone else needs and figure out what you need and make a deal,” he continued. “It’s unfortunate because I think everyone loses in the process.”

Sondland has not publicly addressed the Ukraine controversy and did not respond to a request for comment through the EU embassy in Brussels, Belgium.

While Sondland’s alliances and political giving have trended heavily Republican in recent years, associates described him as more pragmatic than partisan, building relationships with whoever is in power.

“He was a cheerleader for incumbents, he became friends with people who were officeholders. That was his political ideology more than any bedrock conservatism,” said Len Bergstein, a Portland political consultant who worked with Sondland during a long fight against a publicly owned convention center hotel in Portland.

Sondland became a campaign donation bundler for Mitt Romney’s failed 2012 presidential campaign, in part to boost his chances of achieving his dream of a European ambassadorship, said David Nierenberg, an investment manager in Camas, Clark County, who helped lead Mitt Romney’s national finance team.

Sondland “was not reticent” about his pursuit of a diplomatic post, preferring a German-speaking nation, which would have meant a son of Holocaust refugees “would have come full circle,” Nierenberg said. “This is what he wanted and long sought.”

Oregon Democratic Sen. Ron Wyden vouched for Sondland, known in Oregon as “Gordie,” as “a really good fit” during his confirmation hearing last June for the EU ambassador post.

Wyden praised the hotelier’s civic involvement, noting he’d known Sondland’s family for years in Oregon’s relatively small Jewish community. Sondland has frequently donated to his campaigns.

On Friday, Wyden issued a statement saying Sondland “and any official who has knowledge of Trump’s schemes to get foreign leaders to interfere in our elections” should cooperate with the ongoing impeachment inquiry.

“Donald Trump has a long history of throwing his associates under the bus to protect his own skin, and I expect that any Trump official banking on this administration to protect them ought to think seriously about the prospect of major disappointment,” Wyden warned.

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Refugees’ son to hotel magnate

Sondland grew up on Mercer Island, born to Jewish parents who married in Germany when his mother was 15 and then fled to escape the Holocaust.

His dad had been a fur trader, but that business didn’t really exist in Seattle. Both his parents went to Seattle Community College for a year, where they learned the dry-cleaning business, his mother said in a University of Washington oral history project. They bought a West Seattle dry cleaner and ran Fauntleroy Cleaners until they retired in their 70s.

The family was “lower middle class,” Sondland said in the 2016 interview, but lived amid great wealth on Mercer Island.

“You saw some kids on their 16th birthday with the new BMW that their parents bought them and some kids had to walk to school or take the bus,” he said. “It created a lot of interesting dynamics that probably followed me for the rest of my life.”

He went to the University of Washington and later started working in Seattle as a real estate broker. He sold apartment buildings, mainly, “a lot of the little brick buildings on Capitol Hill, Queen Anne Hill.”

Around 1985, a broker who worked for him showed him a bankrupt hotel and asked about how to sell it. Sondland put together an investment group and bought the property himself, paying $7.8 million for the Roosevelt Hotel in downtown Seattle.

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Now known as the Hotel Theodore, it’s appraised at more than $52 million and is one of 14 hotels owned by Provenance Hotels, the boutique chain Sondland founded. The chain includes Seattle’s Hotel Max, Tacoma’s Hotel Murano and six hotels in Portland, including The Heathman.

As his wealth grew, Sondland and his wife, Katherine Durant, built an art collection valued at up to $25 million, according to federal financial disclosures. He’s been a major donor to the Portland Art Museum and the Frye Art Museum in Seattle. Both museums have facilities named after Sondland’s family.

He’s also given to Washington politicians, including Democrats Norm Dicks and Maria Cantwell and Republicans Cathy McMorris Rodgers and Jaime Herrera Beutler in Congress, and Republican Dino Rossi’s 2008 campaign for governor.

With Sondland facing intense scrutiny over his role in the Ukraine affair, his former associates fear his ambition to be a high-ranking diplomat could wind up permanently tarnishing his name.

Nierenberg said in the years he worked with Sondland on political fundraising, “he never said or did anything that gave me any question about his personal ethics.”

But Nierenberg now said he feels “queasy” about what he is reading.

“If I were in a position to provide counsel to Gordon, I would say you are going to be testifying next week: Tell the truth, the whole truth, and nothing but the truth.”

News researcher Miyoko Wolf contributed to this report.