Gordon Sondland Elbowed His Way Into Ukraine Policy.

WASHINGTON — To foreign policy experts, it is no mystery why President Trump’s national security adviser tried in May to block Gordon D. Sondland from becoming a player in United States diplomacy with Ukraine.

As the American envoy to the European Union, Mr. Sondland managed a portfolio unrelated to Ukrainian issues. And beyond that, he was so inexperienced as a diplomat — a wealthy Republican donor rewarded with an ambassadorship — that one top White House foreign policy adviser complained he was a national security risk.

But Mr. Sondland wedged his way into Ukraine policymaking anyway, attending the new president’s inauguration in Kiev in May and briefing Mr. Trump afterward, all over the objections of the national security adviser at the time, John R. Bolton. And now Mr. Sondland’s gambit appears to have placed him at the center of House Democrats’ impeachment inquiry.

In testimony scheduled for Thursday, Mr. Sondland was expected to say that during a meeting in May, Mr. Trump gave him and two other officials the impression that they should coordinate on Ukraine issues with his personal lawyer Rudolph W. Giuliani. That command effectively created a foreign policy back channel that cut the State Department and National Security Council out of deliberations involving a pivotal ally against Russia.

Mr. Sondland was also expected to testify that he realized by midsummer that Mr. Trump had a condition for agreeing to an Oval Office meeting with Volodymyr Zelensky, the new president of Ukraine: an announcement by Ukrainian prosecutors that could benefit Mr. Trump’s political fortunes.

Initially hopeful that Mr. Sondland’s account would help Mr. Trump, congressional Republicans now fear it will add momentum to Democrats’ impeachment inquiry. His decision to testify is itself a sign of fissures in the support for Mr. Trump, evidence that even some defenders have balked at shouldering the legal and reputational costs of thwarting the impeachment inquiry.

Read the Text Messages Between U.S. and Ukrainian Officials

The messages reveal new details about President Trump’s efforts to use American foreign policy to benefit himself.

In a matter of weeks, Mr. Sondland has evolved from a neophyte diplomat known for his ambition and subservience to the president into a witness, however unwilling, in a proceeding against Mr. Trump.

In the process, Mr. Sondland’s own reputation took a hit. Fiona Hill, the former senior director for European and Russian affairs at the White House, described him to congressional investigators this week as a well-meaning but inexperienced liability.

He used his personal cellphone for official business and assured foreign officials they were welcome at the White House whenever they liked, she testified. On one occasion, she said, Romanian officials showed up at the White House gates with no appointment, citing Mr. Sondland.

Experts said his story was an object lesson in the pitfalls of handing influential foreign posts to diplomatic naïfs, while stripping oversight from the career officials at the State Department and the National Security Council.

“I told the Europeans, maybe this is the best you can expect” from the Trump administration, said Daniel Fried, a former longtime diplomat now with the Atlantic Council. No one imagined, he said, that Mr. Sondland would become a pivotal player “in this bottomless pit” of scandal.

Mr. Sondland, 62, tall and bald, is far from a typical diplomat. Foul-mouthed and unafraid to bruise egos, he craves the limelight, not policy papers and the politics of quiet persuasion that are the staples of diplomacy.

He nonetheless fits a certain mold of ambassadors: The founder of a boutique hotel chain, he landed his post after decades of work bankrolling Republican presidential candidates, including John McCain, Mitt Romney and George W. Bush and his brother Jeb Bush. In Bush family circles, he was particularly well liked.

“There aren’t many people who do it as well as he does,” David Nierenberg, an investment manager in Washington State who worked on Mr. Romney’s campaigns, said of Mr. Sondland’s fund-raising prowess. “He knew how to deliver.”

Friends said he loved the trappings of politics: ferrying presidential candidates around the northwest in his Lear jet and hosting their events at his 8,300-square-foot estate in Portland, Ore.

He had hoped to be rewarded, he told Mr. Nierenberg, with an ambassadorship in a German-speaking country. That would bring his life full circle, he explained: His parents fled Nazi Germany as teenagers in 1939.

But he was a latecomer to supporting Mr. Trump, first backing Jeb Bush, then Marco Rubio. During the 2016 campaign, after Mr. Trump disparaged the Muslim parents of an American soldier killed in Iraq, Mr. Sondland and his business partner backed out of a fund-raiser, saying they did not share Mr. Trump’s values.

Those reservations apparently vanished once Mr. Trump was elected. Mr. Sondland donated $1 million to his inaugural committee, joining a crush of once-reluctant donors anxious to make up for their previous lack of support. In spring 2017, he joined the Republican National Committee’s finance committee as a regional vice chairman.

Reince Priebus, Mr. Trump’s first chief of staff, was unwilling to grant Mr. Sondland an administration job. But after Mr. Priebus was fired, Treasury Secretary Steven Mnuchin, who knew Mr. Sondland from the campaign, put forward his name for ambassador, according to people familiar with the situation. He was appointed in May 2018.

By then, the post had gone unfilled for more than a year. Some European officials suspected it was a deliberate sign of neglect of Western allies that Mr. Trump has accused of unfair trade practices.

European officials were struck Mr. Sondland’s self-confidence, bordering on arrogance. He quickly posted an introductory video on Twitter. Set to snappy string music, it described him as the son of immigrants and showed him brewing espresso, showing off his fine art collection and climbing into a private jet that he pilots.

His message to his European hosts was less friendly. At one dinner party, Mr. Sondland said his job was “to destroy the European Union,’’ one senior European official said.

He repeatedly told European officials that their countries had long taken advantage of the United States through trade, according to one person who heard him complain. And he seemed unaware of protocol, inviting the leaders of European countries to dinner without understanding that they do not typically dine with ambassadors.

A June 28 dinner in Brussels was a case study in his unapologetic style. The German Marshall Fund originally organized it for 18 former and current diplomats and academics to discuss trans-Atlantic relations. Once Mr. Sondland heard about it, two participants said, he insisted on hosting.

As the plates were cleared in a small ornate room in the American Embassy, he delivered what one guest described as “a first-year master’s student’s” account of the Marshall Plan, the United States’ multibillion-dollar effort to rebuild Europe after World War II.

“We paid all this money, but every room I go to in Europe, I get told no,” he told his stunned guests, according to two participants. “Why?”

“It felt like a shakedown,” said one of the guests.

European officials said that Mr. Sondland often bragged about his good relationship with Mr. Trump, and some said it was clear that he was looking for a higher-level administration post.

How he inserted himself into American relations with Ukraine, which is not part of the European Union, is not entirely clear. Ms. Hill has said he told her that Mr. Trump had put him in charge.

In a July interview with a Ukrainian television station, Mr. Sondland presented himself as an authority, dismissing the notion that Ukraine is torn between Europe and Russia. “It’s not a tug of war. They’re Western, and they’re going to stay Western,” he proclaimed.

With Mr. Trump’s blessing, he traveled to Kiev in May for Mr. Zelensky’s inauguration. Others in the delegation included the energy secretary, Rick Perry, and Kurt D. Volker, the American special envoy to Ukraine. The three labeled themselves “the three amigos.”

Mr. Sondland’s subsequent White House meetings are a key focus of questioning for congressional investigators.

When he and his colleagues briefed Mr. Trump on May 23, the president complained that the Ukrainians were “all corrupt” and had tried to keep him from winning the White House. He left them with the impression that they were to talk to Mr. Giuliani in dealing with Ukraine.

By mid-July, Mr. Sondland was expected to testify, he had realized that Mr. Zelensky would be granted an Oval Office audience only if Ukraine publicly announced it would investigate Burisma, a Ukrainian energy company that had placed Hunter Biden, the younger son of former Vice President Joseph R. Biden Jr., on its board. But according to a person familiar with his account, Mr. Sondland did not then understand the relationship between Burisma and the Bidens.

In a July 10 White House meeting with Mr. Bolton, Ms. Hill and two top Ukrainian officials, Mr. Sondland cited an agreement with the acting White House chief of staff, Mick Mulvaney, that inviting Mr. Zelensky to the Oval Office depended on Ukraine opening criminal investigations, according to Ms. Hill’s testimony. She told congressional investigators that she subsequently heard Mr. Sondland mention Burisma to the Ukrainians.

Mr. Sondland was expected to testify that he has no firm recollection of that conversation. But the next month, he and Mr. Volker prepared a draft statement for the Ukrainians to issue, announcing an investigation of Burisma and any interference in the 2016 American presidential election. And in a subsequent text message, he wrote: “POTUS really wants the deliverable.”

One person close to Mr. Sondland said he now feared that he would be blamed for the scandal, while more powerful players would be protected. He has expressed concern that he could end up, the person said, as “collateral damage.”

Reporting was contributed by Nicholas Fandos, Adam Goldman and Kenneth P. Vogel from Washington; Steven Erlanger from Brussels; and Maggie Haberman from New York. Kitty Bennett contributed research.

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