BRUSSELS — Gordon D. Sondland, the blunt-spoken hotelier who is President Trump’s ambassador to the European Union, was boasting on Ukrainian television that Mr. Trump had honored him with a “special assignment” — “overseeing” relations between the two countries “at the highest levels.”
Mr. Sondland had arrived in Kiev on July 25, the day of the now-infamous telephone call between President Trump and the new president of Ukraine, Volodymyr Zelensky. He had spoken to Mr. Trump minutes before the call, he said, and met with Mr. Zelensky for an hour the next morning, before his television interview.
At the time, his television remarks might have been the kind of diplomatic bluster one would expect of Mr. Sondland, a big, loquacious man who has been a prominent Republican donor and fund-raiser for years and loves to remind people of the good relationship he has developed with Mr. Trump.
But in the glare of the impeachment inquiry swirling in Washington, Mr. Sondland’s mission is now being scrutinized in an entirely different light, to assess whether it was to give a lift to American relations with Ukraine, or actually to serve as Mr. Trump’s personal fixer.
“We can make sure that all the reforms and all of the initiatives that we are undertaking with Ukraine stay on track and happen quickly,” Mr. Sondland said in the television interview.
What Mr. Sondland did not say, and what has become clear in the messages released on Thursday
In return, Mr. Zelensky would get the White House meeting he craved and, implicitly, Washington would release military aid held up on Mr. Trump’s request.
[Ukraine says it will review a criminal case on the owner of a firm linked to Biden’s son]
Asked in the interview about progress in Ukraine-America relations, including questions like membership of NATO and energy security, Mr. Sondland urged patience.
“It’s not a question of saying no,’’ Mr. Sondland said of the Zelensky government. ‘‘It’s a question of saying when. There are certain things that they have to do. There are preconditions to anything.”
Mr. Sondland also spoke to Ukraine’s state-run news agency after the call and said: “The conversation was very successful. They found a common language immediately.” He said the two leaders discussed Ukraine’s war, energy security and “the rule of law.”
Mr. Sondland, 62, arrived in Brussels as ambassador to the European Union in June of last year, having raised a lot of money for Mr. Trump after building a lucrative hotel chain in the Pacific Northwest.
He sees his job as pressing Mr. Trump’s agenda, which is tightly focused on trade and the impediments that lead to a $151 billion trade deficit in goods with the European Union, a figure Mr. Sondland often cites.
Mr. Sondland has said that his grandparents were from Ukraine. His parents were both refugees from the Nazis, and he was the first in his family to be born in the United States.
In September 2018, Mr. Sondland posted a video to introduce himself and his family to Europeans, featuring shots of him making coffee, relaxing at home, showing off his collection of art, climbing into a jet that he likes to pilot, and walking his dogs on the beach with his wife, Katherine Durant, a businesswoman, and introducing his son Max and daughter Lucy.
Ms. Sondland backed out of hosting a fund-raiser for Mr. Trump in 2016, citing Mr. Trump’s disparaging comments toward immigrants and the family of a slain Muslim-American soldier. But in the end Mr. Sondland donated $1 million through his companies to the inaugural committee for Mr. Trump.
That relationship seems to have led to his apparent responsibility in Ukraine after the previous ambassador, Marie L. Yovanovitch, a career diplomat, displeased the White House and was removed several months before the end of her term.
Mr. Sondland’s “special assignment” from Mr. Trump was never formally announced, but it was instrumental in the negotiations with Mr. Zelensky’s team and Rudolph W. Giuliani, the president’s personal lawyer, who was pressing for these essentially political investigations.
Officials in Mr. Sondland’s embassy say that the Ukrainian effort was not a part of their own work with the European Union, and that they were not aware of the extent of Mr. Sondland’s activities in Ukraine.
In his interview with Ukrainian television, Mr. Sondland said the American-Ukrainian relationship was in the hands of “what are called the three amigos’’ — himself, Energy Secretary Rick Perry and Kurt D. Volker, the special representative for Ukraine negotiations.
Mr. Sondland arrived in Kiev the day of the phone call, on July 25, and has said that he spoke to Mr. Trump minutes before the call took place, and then met with Mr. Zelensky for an hour the next morning along with Mr. Volker, who quit his role after the whistle-blower’s complaint about the call was made public.
The whistle-blower has described the two men as having “reportedly provided advice to the Ukrainian leadership about how to ‘navigate’ the demands that the president had made of Mr. Zelensky.”
In a message to a Zelensky adviser on July 25, ahead of the call, Mr. Volker said he was assured by the White House that if Mr. Zelensky could convince Mr. Trump that he “will investigate / ‘get to the bottom of what happened’ in 2016, we will nail down date for visit to Washington.”
That message made no reference to Mr. Biden or his son, just to Mr. Trump’s conviction that 2016 election meddling came from Ukraine, not Russia. Nor did it mention the frozen military aid.
Mr. Sondland has declined to comment, referring all questions to the White House. But he seems from the messages to have been instrumental in trying to get Mr. Trump what he wanted in a fashion that would get Mr. Zelensky the White House meeting he wanted, as well as the unfreezing of the military aid.
From the messages released, the acting ambassador to Ukraine, William B. Taylor Jr., a career diplomat who had previously been ambassador to Ukraine from May 2006 to May 2009, was extremely uncomfortable with the implicit quid pro quo insisted upon by the White House.
Ukrainian “faith” in Washington was already shaken by the withholding of aid, Mr. Taylor said in a message to Mr. Sondland, and if in the end Ukraine made the statement Mr. Trump wanted and was denied the military assistance anyway, Mr. Taylor messaged, “the Russians love it. (And I quit.)”
Mr. Sondland’s predecessor, Anthony L. Gardner, appointed by President Barack Obama, said that such a special assignment to Ukraine was “extremely unusual,’’ since it has little to do directly with the European Union.
But Mr. Sondland told reporters last month that he saw Ukraine as among a handful of “low-hanging fruit” areas of policy where the European Union could work together with Washington.
The July visit was the third Mr. Sondland made to Ukraine. He was in Odessa in February and in Kiev again in May, when he attended Mr. Zelensky’s inauguration, which Vice President Mike Pence was ordered not to attend by Mr. Trump.
Instead, the delegation was led by Mr. Perry and included Mr. Volker, Mr. Sondland and Senator Ron Johnson, Republican of Wisconsin. They then briefed Mr. Trump in the White House about Mr. Zelensky and his eagerness to combat corruption, but Mr. Trump was not convinced.
Mr. Sondland continued building a relationship with Mr. Zelensky, hosting him at a June dinner at the United States mission to the European Union in Brussels after a July 4 party that featured Jay Leno, who is a friend of Mr. Sondland.
The party and the dinner was also attended by Jared Kushner, Mr. Trump’s son-in-law and adviser; Mr. Perry; the Polish prime minister; and Ulrich Brechbuhl, a State Department counselor who is mentioned in the whistle-blower memo as having listened in to the July 25 telephone call.
On Aug. 9, according to the texts released, Mr. Sondland thought he was finally making progress on getting a date for the Zelensky visit to the White House. But he was unsure, messaging Mr. Volker: “I think POTUS really wants the deliverable,” meaning a public Zelensky statement about his commitment to investigate the Bidens and 2016.
Even though the Ukrainians seemed to agree, Mr. Trump still would not set a date for a meeting.
Mr. Perry, Mr. Sondland and Mr. Pence also met with Mr. Zelensky in Warsaw on Aug. 31, when Mr. Trump canceled his own visit, citing a hurricane. That meeting appeared routine, according to Mr. Perry’s readout.
“The Vice President reiterated the U.S.’ support of Ukraine’s security and rightful claim to Crimea,’’ the statement read. ‘‘President Zelensky articulated his administration’s commitment to defeating corruption and pledged to launch much anticipated reforms.”
On Sept. 1, Mr. Taylor texted Mr. Sondland: “Are we now saying that security assistance and WH meeting are conditioned on investigations?” Mr. Sondland responded by ending the text exchange and reverting to a telephone call.
But by Sept. 9, matters remained unclear. Mr. Taylor, the acting ambassador, messaged: “As I said on the phone, I think it’s crazy to withhold security assistance for help with a political campaign.”
Mr. Sondland responded: “Bill, I believe you are incorrect about President Trump’s intentions. The President has been crystal clear no quid pro quo’s of any kind.’’