How Gordon Sondland Went From Trump Critic to Trump's Ukraine Whisperer

UPDATE 10/11: Gordon Sondland has now agreed to testify in front of Congress — and defy the Trump administration in the process. “Notwithstanding the State Department’s current direction to not testify, Ambassador Sondland will honor the Committees’ subpoena, and he looks forward to testifying on Thursday,” Sondland lawyers Robert Luskin and Kwame Manley said in a statement.

When Gordon Sondland, U.S. ambassador to the European Union, dropped by Ukrainian state television for an interview last July, the host seemed a little confused by his visit.

“You’re the U.S. ambassador to the EU, but you’ve been spending a great deal of time in Kiev,” reporter Kari Odermann asked Sondland. “Why is that?”

“Well, President Trump has not only honored me with the job of being the U.S. ambassador to the EU,” Sondland responded. “But he has also given me other special assignments — including Ukraine.”

Odermann can be forgiven for the confusion. Sondland’s path to the diplomatic post is rather odd: He’s a wealthy former hotel and finance magnate turned political donor turned globetrotting diplomat.

But even more mysterious is his involvement in the affairs of Ukraine, a non-EU country, where he’s made at least three separate visits in recent months. It’s a mystery that House investigators are trying to solve, but they won't be able to ask Sondland about it: On Tuesday, hours before he was due to answer questions in a closed-door hearing, the Trump administration told him not to testify.

"Early this morning, the U.S. Department of State directed Ambassador Gordon Sondland not to appear today for his scheduled transcribed interview," Sondland's attorney said in a statement. "Ambassador Sondland is profoundly disappointed that he will not be able to testify today."

Sondland has quickly emerged as a key figure in the House’s ongoing impeachment investigation. He was mentioned in the complaint of the anonymous intelligence-community whistleblower, who said Sondland helped “‘navigate’ the demands that the president had made of" Ukrainian President Volodymyr Zelensky.

And last Thursday, Kurt Volker, former U.S. acting ambassador to Ukraine, provided House investigators text messages that show Sondland acted as a conduit for Trump with Ukraine’s new government, helping set up the July 25 call in which Trump asked Zelensky to investigate former Vice President Joe Biden and his son Hunter.

"We know Ambassador Sondland was a key player in efforts to obtain the commitment from Ukraine to investigate a bogus conspiracy theory about the 2016 election as well as Joe Biden and his son," House Intelligence Committee Chairman Adam Schiff (D-Calif.) said Tuesday morning.

Sondland is the son of German Jews who escaped the Holocaust and eventually settled in the Pacific Northwest. He’s a diehard conservative who once gifted his wife a signed copy of Ayn Rand’s "Atlas Shrugged."

He made a fortune in the hotel industry and has been a major GOP donor for decades. But the extent of his actual governmental experience had been limited to work on an Oregon state board that sought to bring television and movie production to the state, plus a spot on the ceremonial Commission on White House Fellows during George W. Bush’s presidency.

He backed former Florida Gov. Jeb Bush in the 2016 GOP primary, donating more than $20,000 to a pro-Bush superPAC. He came around once Trump was the de facto nominee, with plans to chair a fundraiser. But then he pulled out when Trump attacked the family of Humayun Khan, a Muslim-American soldier who’d died in the line of duty.

A Sondland spokeswoman said at the time that Sondland and his business partner, Bashar Wali, were done with Trump.

“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, and Mr. Wali is a Muslim-American who emigrated to this country from Syria,” Provenance Hotels spokeswoman Kate Buska told Willamette Week. “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.”

But for Sondland, those values were apparently malleable. After Trump’s victory, Sondland gave a combined $1 million to Trump’s inaugural committee through four limited liability corporations, as first reported by the Center for Responsive Politics.

That put him back in the president’s good graces. Early last year, Trump nominated him to be EU ambassador.

Sondland has talked up how close he is to the president. During that Ukrainian TV interview, he said he’d talked to Trump before sitting down with Ukraine’s president. But he may end up regretting his newfound role in Trump’s inner circle.

Sondland would certainly have been asked about that interview, which came the day after Trump’s now-famous call with Ukraine’s president. “We want to make sure that all of the reforms are on track,” he said, an apparent reference to Trump’s push to get Ukraine to investigate debunked theories that Ukraine meddled in the 2016 election — and perhaps Biden.

Investigators surely also have questions about Sondland’s text messages, which reveal his efforts to help Trump secure the Ukraine government’s cooperation. The president has publicly called for Ukraine to investigate Biden after doing so during his call with Zelensky in late July.

“I think POTUS really wants the deliverable,” Sondland texted Volker on Aug. 9. In the same conversation, he suggested asking to see a draft statement on what Ukraine’s president would say to ensure it matched what Trump was pushing for — an investigation into who was behind 2016.

Acting U.S. Ambassador to Ukraine Bill Taylor texted Sondland on September 9 saying “it's crazy to withhold security assistance for help with a political campaign.” Sondland fired back hours later, insisting that “no quid pro quo's of any kind” were promised — before asking Taylor to stop texting about the issue.

Former diplomats told VICE News that Sondland’s “special assignment” was unusual.

“It’s out of the ordinary to have another ambassador intervening in a random country,” said Gordon Giffin, who served as U.S. ambassador to Canada under President Clinton.

Two previous U.S. ambassadors to the E.U. said issues related to Ukraine did come up at times in the course of their diplomatic work. But both told VICE News they never visited the country during their assignment.

Boyden Gray served as U.S. ambassador to the EU under President George W. Bush. He told VICE News that Ukrainian energy independence issues had long been part of discussions for EU ambassadors, and said “it’s hard to see [Sondland] not getting involved” in some form with Ukraine.

Tony Gardner, who served in the same capacity under President Obama, said he’d worked on Ukraine-related issues as well, helping coordinate U.S.-EU sanctions against Russia in response to their invasion of Crimea in 2014. But he said he “never traveled to Kiev” while he was in office.

Sondland didn’t respond to a phone call requesting comment. Buska and Wali also didn’t respond to requests for comment. Nor did the White House.

Sondland sailed through his Senate confirmation process with bipartisan support. Sen. Ron Wyden (D-Ore.) even vouched for his fellow Oregonian during the confirmation hearing. He’d known “Gordy” and his family for a quarter-century in Oregon’s small Jewish community, he said, and praised him for his philanthropic efforts in their state while promising he’d be “a really good fit” for the ambassadorship.

But in light of recent events, Wyden had a warning for his old friend.

“Mr. Sondland, and any official who has knowledge of Trump's schemes to get foreign leaders to interfere in our elections, must fully cooperate with the House Intelligence Committee and the Inspector General,” Wyden said in a statement to VICE News. “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.”

Cover: Gordon Sondland, the U.S. ambassador to the European Union, second from right, with President Trump. (AP Photo/Pablo Martinez Monsivais, File)