When President Donald Trump picked Gordon Sondland as his ambassador to the European Union in March 2018, the nomination was seen as improbable. The self-made millionaire hotel magnate and longtime Republican donor had disavowed Trump's candidacy during the 2016 campaign because of his anti-immigrant rhetoric.
But after Trump won the election, Sondland gave $1 million to the president-elect's inaugural committee, according to the Center for Responsive Politics. That paved the way for his coveted ambassadorship in Brussels, where he oversaw U.S. relations with the 28-member bloc and attended meetings on Ukraine.
Because Ukraine is not a member of the EU, Sondland's deep involvement in U.S. policy toward Ukraine has raised eyebrows. Sondland, however, has defended his role, saying he viewed his work on Ukraine as "central to advancing U.S.-EU foreign policy."
Now, Sondland finds himself in a pressure-packed and pivotal role as the star witness of this week's congressional impeachment hearings beginning Wednesday morning. His testimony could solidify or undermine House Democrats' case against Trump.
That's because Sondland, despite Trump's assertion to the contrary, had a direct line to the president and was intimately involved in the events surrounding the July 25 call between Trump and Ukrainian President Volodymyr Zelenskiy that triggered the impeachment inquiry.
Trump is accused of using the call to try to pressure Zelenskiy to open an investigation into Democratic rival Joe Biden, and Biden’s son, Hunter, at the same time Trump had frozen nearly $400 million in military assistance.
Along with Kurt Volker, the former special envoy to Ukraine, and Rick Perry, the energy secretary, Sondland was a member of a group that dubbed itself the "three amigos," the troika of officials Trump directed to run his unofficial Ukraine policy in concert with Rudy Giuliani, the president's personal lawyer.
When he testified to House committees behind closed doors last month, Sondland sought to minimize his role in the shadow diplomacy, insisting that he played "a support role" rather than a "leadership role" on Ukraine policy.
He also played down his ties to Trump and quashed suggestions that he was taking orders from Trump rather than from Secretary of State Mike Pompeo.
But testimony by other officials has shown that Sondland was in frequent contact with Trump around the time Trump spoke with Zelenskiy. Tim Morrison, the former top Russia and Europe adviser on the National Security Council, testified last month he understood that Sondland had talked to Trump about half a dozen times.
Trump has sought to distance himself from Sondland, saying he hardly knows him.
As Sondland put it during his testimony, a turning point in his involvement in Ukraine came on May 23 when the troika met with Trump in the Oval Office and urged him to call or invite Zelenskiy to the White House in a show of support for Ukraine.
Trump was not interested, asking the trio to talk to Giuliani, Sondland recalled.
"He just kept saying, "Talk to Rudy. Talk to Rudy," Sondland testified.
By then, Giuliani, working with two Soviet-born emigres, had orchestrated a successful campaign to oust the Obama-appointed U.S. ambassador to Ukraine, Marie Yovanovitch, and intensify efforts to pressure the newly elected Ukrainian president into carrying out investigations against the Bidens to delve into their past dealings with Ukraine — including Hunter Biden's lucrative position with the Burisma natural gas company.
In his testimony, Sondland described the sequence of events during the summer as a "continuum," starting with Trump urging the group in May to talk to Giuliani, to Sondland realizing in September that Trump's demand for probing Burisma had amounted to a political investigation into the Bidens.
"It kept getting more insidious as (the) timeline went on," Sondland testified. "And back in July, it was all about just corruption."
Sondland struggled to recall key events in the Ukraine affair, including whether he had told a Ukrainian official that U.S. military aid was tied to Ukraine carrying out the investigations requested by Trump.
When he takes the witness stand for a second time on Wednesday, Sondland is likely to be grilled over another major oversight — his failure to disclose calling Trump the day after the July 25 phone call between Trump and Zelenskiy.
Democrats say the phone call underscores Sondland's close ties to Trump and puts Trumps close to the heart of the pressure campaign on Ukraine.
David Holmes, a senior diplomat at the U.S. Embassy in Kyiv, overheard the conversation while sitting next to Sondland at a restaurant in the Ukrainian capital.
"So, he's gonna do the investigation?" Trump asked Sondland, according to Holmes.Sondland replied, "He's gonna do it," and that Zelenskiy would do "anything you ask him to," according to Holmes's testimony.
A second embassy staffer reportedly also overheard the cellphone conversation.
