Gordon Sondland, the U.S. ambassador to the European Union, had barely been on the job for a year when he found himself knee-deep in negotiations with the Ukrainian president over President Trump’s desired political investigations.

For weeks leading up to an explosive whistleblower’s complaint, Sondland, a wealthy hotelier from Portland, Ore., worked behind the scenes to carry out Trump’s wishes in a country that’s not part of the European Union. The ambassador met with Ukraine President Volodymyr Zelensky to give “advice” about how to “navigate” Trump’s demands, the whistleblower reported. And in text messages turned over to House investigators Thursday, Sondland insisted that Trump’s decision to withhold nearly $400 million in military aid to Ukraine was not a quid pro quo — as diplomat William B. “Bill” Taylor had feared, according to the texts.

“Bill, I believe you are incorrect about President Trump’s intentions,” Sondland wrote last month, before urging Taylor, the U.S. charges d’affaires in Ukraine, to call him instead.

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Those text messages are now at the center of the House impeachment inquiry into Trump’s dealings with Ukraine, bringing State Department officials’ private discussions surrounding the events into sharp focus. But unlike longtime diplomats such as Taylor, Sondland charted an unconventional course on his journey into the middle of the scandal now plaguing Trump’s presidency.

In some ways, Sondland’s path into politics resembles Trump’s: Before his Senate confirmation in June 2018, Sondland was a savvy businessman, the founder and chief executive of Provenance Hotels in the Pacific Northwest whose government experience was limited to chairing the Oregon Governor’s Office of Film & Television and working on Democratic governor Ted Kulongoski’s transition team. The hotel executive’s support for Trump had ebbed and flowed over the years, ranging from outright disavowal during Trump’s campaign to a $1 million donation ahead of Trump’s inauguration.

Now, Sondland’s support for Trump, at least in the text messages revealed Thursday, comes amid the most pivotal moment of his presidency — possibly putting Sondland’s own future in the administration in jeopardy. Former U.S. special envoy to Ukraine Kurt D. Volker, who worked behind the scenes with Sondland and provided their texts to House investigators during closed-door testimony Thursday, has already resigned.

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An attorney for Sondland declined to comment early Friday.

Sondland, a son of Jewish parents who escaped persecution in Nazi Germany, got his start in the hotel business while he was a real estate broker in Seattle in 1985, when he decided to purchase a bankrupt hotel. After that, “I never looked back,” he told the Portland Business Journal in 2016.

His chain of boutique hotels — known for celebrating local art and culture while retaining the history of the original buildings — proliferated across the country. From Tacoma, Wash., to New Orleans, his company owns or operates 19 luxury hotels, each with distinct themes.

Over the years, he established himself as a generous Republican donor, taking on fundraising roles for the Republican National Committee and presidential candidates including Mitt Romney, John McCain and President George W. Bush, who also appointed him to serve on the Commission on White House Fellows, Politico reported.

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He initially supported Jeb Bush in the 2016 presidential campaign, before turning to Trump, the Oregonian reported — but the support didn’t last.

On Aug. 5, 2016, the Seattle Times revealed that Bashar Wali, the president of Provenance Hotels, would host a fundraiser for Trump that month. Just two days later, Sondland and Wali publicly denounced Trump, citing irreconcilable differences in values and beliefs, the Willamette Week reported. A spokeswoman for Provenance Hotels told the paper they didn’t give the Trump campaign permission to list them as hosts of the event, and that they refused to participate.

The two hoteliers pointed to Trump’s criticism of Khizr and Ghazala Khan, the parents of Muslim American soldier Humayun Khan who died serving in the U.S. Army, as a reason for their disdain.

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“Mr. Sondland is a first generation American whose parents were forced to flee Germany during the years leading up to World War II because they were persecuted for their faith,” the spokeswoman, Kate Buska, told the Willamette Week, “and Mr. Wali is a Muslim American who emigrated to this country from Syria.

“Historically, Mr. Sondland has been supportive of the Republican party’s nominees for President,” she continued. “However, 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 disdain would apparently not last for long.

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In 2017, Sondland donated $1 million to Trump’s inauguration committee through four of his limited liability companies. Trump nominated him to be U.S. ambassador to the E.U. the following year.

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The new ambassador quickly took up Trump’s major grievances with other world leaders, urging European leaders to make a better trade deal so they could take on China together. But starting in at least July of this year, according to the text messages, Sondland was working to forward Trump’s interests in Ukraine.

“I [spoke] directly to Zelensky and gave him a full briefing. He’s got it,” Sondland wrote in a group text to Volker and Taylor six days before Trump’s phone call with the Ukrainian president that is at the center of the impeachment inquiry.

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The texts released Thursday appear to show multiple State Department officials — including Sondland and Volker — seeking to lock down Zelensky’s promise to launch an investigation into the 2016 election and into a natural-gas company that previously employed former vice president Joe Biden’s son Hunter. Hanging in the air was a potential meeting between Trump and Zelensky that the Ukrainian president badly wanted.

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Taylor, by contrast, was skeptical.

“Gordon,” he wrote on July 21, four days before Trump’s phone call with Zelensky, “one thing Kurt [Volker] and I talked about yesterday was … that President Zelenskyy is sensitive about Ukraine being taken seriously, not merely as an instrument in Washington domestic, reelection politics.”

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“Absolutely,” Sondland responded, “but we need to get the conversation started and the relationship built, irrespective of the pretext. I am worried about the alternative.”

At one point, Andrey Yermak, an aide for Zelensky, appeared ready to agree to have Zelensky publicly announce that the Ukrainians would launch Trump’s desired investigations — but only once a date for the meeting between the two leaders was settled, the text messages show. Sondland went so far as to consider requesting that U.S. officials have prior review of the Ukrainian officials’ public statement announcing the supposed investigation, according to the text messages.

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But that never happened. After news broke in late August that Trump had withheld $391 million in military aid to Ukraine, Trump also canceled a meeting scheduled with Zelensky in Poland. Taylor grew more concerned.

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“Are we now saying that security assistance and WH meeting are conditioned on investigations?” Taylor asked Sondland on Sept. 1.

“Call me,” Sondland responded.

Taylor later described fearing a “nightmare scenario” in which the Ukrainians give what Trump wants but do not get the security assistance in return. “As I said on the phone,” he told Sondland on Sept. 9, “I think it’s crazy to withhold security assistance for help with a political campaign.”

That’s when Sondland told him he believed he was wrong.

“The President has been crystal clear no quid pro quo’s of any kind,” Sondland wrote. “The President is trying to evaluate whether Ukraine is truly going to adopt the transparency and reforms that President Zelensky promised during his campaign.”

With that, Sondland said it would be better to stop texting about the issue.

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