The first major face-off between Trump and the House of Representatives over the impeachment inquiry centers on the unlikely figure of Gordon Sondland.

Before the Ukraine scandal broke, Sondland was little known outside diplomatic circles (he’s the US Ambassador to the European Union) and the Pacific Northwest (where he was a prominent hotelier and political donor).

Yet reports and text messages have revealed that Sondland was deeply involved in President Donald Trump’s effort to get Ukraine to launch investigations into the Bidens and into circumstances around the 2016 election.

One Republican senator even claims Sondland told him Trump was withholding military aid from Ukraine until they agreed to do those investigations. And when a diplomat voiced concern about this, Sondland urged him not to text about the matter but rather to talk about it on the phone (which would leave no record of what was discussed).

A curious question in all this is why Sondland, whose ambassador post is based in Brussels, was involved in Ukrainian diplomacy in the first place, given that Ukraine is not in the EU. But President Trump reportedly wanted him involved. Trump often gave him “special assignments,” Sondland has claimed, “including Ukraine.” Sondland’s donation of $1 million to Trump’s inauguration may have helped buy him the president’s ear. And a trove of text messages turned over to Congress last week makes clear he’s at the center of the effort to pressure Zelensky.

Naturally, House Democrats were eager to hear from Sondland and to get messages on a personal device that Sondland said he had. But in the early hours of Tuesday morning, the Trump administration stepped in and instructed Sondland not to appear for a closed-door deposition scheduled for later that day. That won’t end the story, though, since Democrats then subpoenaed Sondland, instructing him to appear and testify by next week.

Who is Gordon Sondland?

A developer and luxury hotel magnate from the Pacific Northwest, Sondland has been a donor and an influential player in Oregon and Washington state politics for decades. He is quite wealthy; last year, he disclosed owning a Lear Jet and an art collection he valued between $5 million and $25 million. Locally, he exerted influence on past Democratic governors in Oregon (despite living in Portland, he declared his residence to be in Seattle in order to avoid taxes). Nationally, though, he’s been a solid Republican, giving regularly to the party’s presidential nominees.

So when Donald Trump won the Republican Party’s presidential nomination in 2016, it seemed that Sondland would join his team as well: a fundraiser invitation that August named Sondland as the Oregon and Washington co-chair of the Trump Victory committee. But when the press started asking questions about this, Sondland dropped Trump like a hot potato.

At the time, Trump was embroiled in controversy due to his bigoted attacks on the Muslim parents of a slain US soldier who spoke at the Democratic convention. “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,” a spokesperson for Sondland’s hotel company said in a statement. Because of Trump’s “treatment of the Khan family,” the spokesperson continued, Sondland could not “support” Trump’s candidacy.

This supposedly principled stance was quickly abandoned by Sondland once Trump won. Despite no known changes to Sondland’s ancestry or Donald Trump’s behavior, Sondland decided to give $1 million to Trump’s inaugural committee. But he obscured those donations by having them sent through four LLCs rather than under his name, in an apparent attempt to avoid bad press for his flip-flop.

Sondland’s ambition seems to have been to upgrade himself from a regional power player to a national one. And he got what he paid for. In May 2018, President Trump announced he would nominate Sondland as the US Ambassador to the European Union, and he was confirmed by the Senate without objection the following month. He of course had no diplomatic or federal government experience, but doling out plum ambassador gigs to rich donors is a common bipartisan practice.

Sondland didn’t seem to be a great ambassador to the EU, but Trump had other priorities

As a new ambassador, Sondland quickly “garnered a reputation for his truculent manner and fondness for the trappings of privilege,” according to a dishy report by the Washington Post’s Greg Miller, Paul Sonne, Greg Jaffe, and Michael Birnbaum. The Post report revealed:

Sondland seemed to have little interest in doing his actual job in Brussels, instead gallivanting off to various other countries “with little or no coordination with other officials.”

He “acquired a reputation for being indiscreet,” including for using his personal phone for official business.

He frequently threw Trump’s name around and claimed he was acting at the president’s behest.

And he brought a wireless buzzer into meetings to “silently summon support staff to refill his teacup.”

So, he’s a somewhat ridiculous and absurd figure. But he claimed to have Trump’s ear — which would make sense, due to that $1 million inaugural contribution. “President Trump has not only honored me with the job of ambassador to the EU, but he’s also given me other special assignments,” Sondland has said, adding, “including Ukraine.”

The Three Amigos

By the spring of 2019, Trump’s personal lawyer Rudy Giuliani had been fixated on Ukraine for months and had particularly been trying to get their prosecutor general to launch investigations into Trump’s political opponents. Those plans, however, were spoiled by Volodymyr Zelensky’s victory in Ukraine’s presidential election in April. This meant a new regime was coming in — and a new set of people would have to be pressured.

So in May 2019, the State Department recalled the US ambassador to Ukraine, Marie Yovanovitch — apparently because Giuliani and other outside Trump allies were agitating for her ouster, viewing her as politically unreliable. (She had not been helpful to Giuliani’s dirt-digging efforts.)

This made Bill Taylor, a State official who’d had a lengthy career in diplomacy, the top-ranking US diplomat in Kyiv until Trump could get a successor confirmed. But Taylor wasn’t a Trump guy and would be unlikely to aid an effort to skew policy to serve Trump’s political interests (as events would later prove).

So, as Sondland would later explain to a Ukrainian interviewer, Trump instead “tasked” three other people with “overseeing the Ukraine-US relationship.” First, and apparently running the show, was Sondland himself. The other two were Kurt Volker, the part-time, unpaid US special representative for Ukraine; and Rick Perry, the Secretary of Energy. Sondland referred to them as “The Three Amigos.”

By all accounts, the three amigos genuinely wanted to bring the US and Ukraine closer together. There were strategic reasons to do so (checking Russia’s influence) as well as financial ones (there was money to be made from natural gas deals with Ukraine). The roadblock, though, was President Trump himself, who professed to have a grudge against the “corrupt” country.

And the way to remove that roadblock? Well, Ukraine would have to please Trump by investigating both the Bidens and supposed Ukraine interference in the 2016 election. Trump told the amigos in May that, for Ukraine to make him happy, they’d have to make Giuliani happy, according to CNN.

Sondland understood the quid pro quo

As the summer went on, Sondland continued to take an active role in the US-Ukrainian relationship. The Post reported that President Zelensky, Jared Kushner, and comedian Jay Leno were among Sondland’s guests at a private dinner in Brussels in early June. Sondland also attended an early July White House meeting with Ukrainian officials and seemed to allude to the demand for investigations.

His efforts to arrange a phone call between Trump and Zelensky went into high gear in July. On July 19, Sondland texted Volker: “Looks like Potus call tomorrow. I [spoke] directly to Zelensky and gave him a full briefing. He’s got it.”

But the call didn’t happen for a few more days. In that timespan, Bill Taylor (the top US diplomat in Ukraine) mentioned that Zelensky was worried about being used “as an instrument in Washington domestic, reelection politics” — an apparent allusion to the investigations.

Sondland answered: “Absolutely, but we need to get the conversation started and the relationship built, irrespective of the pretext.”

The call took place on July 25, and Trump made clear he wanted Zelensky to investigate the Bidens and the 2016 election. A few weeks later, Sondland mentioned to Volker that “I think potus really wants the deliverable” and hatched the idea that Zelensky could make a statement, reviewed by the Trump team in advance, announcing the investigations Trump wanted. The Ukrainians, however, never committed to making such a statement.

In late August, the situation escalated, when Politico reported that Trump was blocking hundreds of millions of dollars in military aid to Ukraine. Shortly afterward, Sen. Ron Johnson (R-WI) claims that Sondland told him the aid was being held up unless Ukraine agreed to launch those investigations.

This, it turned out, was not a topic Sondland wanted to discuss via text message. “Are we now saying that security assistance and WH meeting are conditioned on investigations?” Bill Taylor texted Sondland on September 1.

Sondland’s only response that day was “Call me.” But he remained deeply involved in the issue. On September 8, he texted Volker and Taylor that he’d had “multiple convos with Ze, Potus” on the topic.

The four-and-a-half-hour gap

But by September 9, the aid was still held up and Taylor was becoming more and more frustrated. He’d already threatened to quit if the Ukrainians didn’t get the security assistance. Sondland’s new idea, it seems, was to have Zelensky give an interview of some kind (the details here are unclear).

“Counting on you to be right about this interview, Gordon,” Taylor texted.

Sondland answered: “Bill, I never said I was ‘right.’ I said we are where we are and believe we have identified the best pathway forward. Lets hope it works.”

But then Taylor went further. “As I said on the phone, I think it’s crazy to withhold security assistance for help with a political campaign,” he wrote.

This text likely alarmed Sondland. With it, Taylor put in writing an objection he says he made on the phone: that Ukraine aid was being linked to help for Trump’s reelection.

Four and a half hours passed before Sondland responded — and in that timespan, Sondland called President Trump. After consulting Trump, Sondland sent a now-infamous response that echoes White House talking points and reads as designed for public consumption.

So, after calling Trump, Sondland laid out what has since become Trump’s favorite talking point: “no quid pro quo’s.” He also took a stiff, formal tone in claiming Trump really, truly wants to evaluate whether Ukraine will embrace reform. And then he sends, in stronger words this time, a warning not to text about this anymore: “I suggest we stop the back and forth by text.”

Two days later, the White House let the military aid for Ukraine go through. Two days after that, news of the whistleblower scandal reached the public for the first time.

The Trump administration blocked Sondland from testifying

So Sondland is in the center of all this and was in contact with both Trump and Zelensky throughout this saga. In theory, he could shed more light on what, exactly, happened.

In particular, one of the ugliest parts of this scandal — the allegation that Trump blocked $400 million in military aid for Ukraine as part of this pressure campaign — is still disputed. We know Trump blocked the aid, but we haven’t quite seen smoking-gun proof that it was part of a quid pro quo for investigations — perhaps because Sondland didn’t want to talk about it via text message.

So, House Democrats got Sondland’s agreement to appear voluntarily at a closed-door deposition Tuesday. But in the early hours of Tuesday morning, the State Department instructed Sondland not to show up to the deposition after all — and he complied, saying that while he was happy to testify and had in fact flown to the US to do so, he was a State Department employee and had to respect the Department’s wishes.

So was the administration afraid of what Sondland would reveal? He is a close Trump ally so he might be predisposed to shade his testimony to protect the president. But that loyalty has not exactly been constant (considering his disavowal of Trump during the 2016 campaign) and he doesn’t seem the type to risk prison by lying for Trump.

That loyalty may be tested again. House Democrats subpoenaed Sondland Tuesday evening, calling on him to give them documents by Monday, October 14, and appear at a deposition on Wednesday, October 16. But around the same time, White House Counsel Pat Cipollone announced that the Trump administration would refuse all cooperation with the impeachment inquiry, which means Sondland is caught in the middle. If Democrats decide to go to court to try and force his testimony, he could be their first test case.