Gordon Sondland, Ex-Portland Hotelier and Self-Proclaimed “Doofus,” Seeks Redemption in Washington Post Profile

The former diplomat is betting that America still loves people who repent.

Imagine you stumble into diplomatic spat, and then you help turn it into a crisis.

Then, imagine you write a book about the crisis, which results in an extensive interview with The Washington Post. The paper tells your story, but instead of making you look good, it calls you “a walking asterisk, a footnote that was once a headline, a man who made some history without really changing the course of it.”

Worse yet, in the story, someone calls you a “doofus.” Worse yet, that person is you, talking about yourself.

That’s exactly what happened to Gordon Sondland, former owner of the company that controlled Portland’s iconic Heathman Hotel, the Sentinel, the Woodlark, Hotel Lucia, Hotel Deluxe and Dossier. He sat for an interview with Post reporter Dan Zak, perhaps following the old adage: “Tell your story, or someone else will.”

Sondland might have been better off keeping quiet.

His troubles began when he got involved with Donald Trump. After some misgivings, Sondland jumped on the Trump Train around 2016 and rode it until it derailed. Trump named him ambassador to the European Union, where Sondland served from 2018 to 2020. During that time, Trump allies, including former New York Mayor Rudy Giuliani, worked to arrange a deal whereby Ukraine agreed to investigate Joe Biden in exchange for a visit to the White House by President Volodymyr Zelensky.

That episode brought Sondland his 15 minutes of fame, just enough to turn himself into a pariah, at least in liberal Portland, where people marched around the Heathman holding signs and shouting for Sondland to tell the truth in his much-anticipated testimony during President Donald Trump’s first impeachment.

In the glare of the House chamber, Sondland acknowledged that Trump had demanded the quid pro quo. He also copped to telling Trump that Zelensky “loves your ass” on a call from Kyiv. That candor, rare for a devoted Trumpist, probably cost him his job. The Senate acquitted Trump on Feb. 5, 2020. Two days later, Trump fired Sondland as ambassador to the European Union.

Sondland is a different man these days. He sold his interest in the local hotels, got a divorce and, like other rich guys with a windfall coming, moved to Florida from the Pacific Northwest to avoid, again in his own words, “taxes.”

In the Post interview, Sondland sounds contrite at times. Pressed by Zak about trying to coerce a foreign government into investigating a political rival for a sitting president, Sondland says: “My own mistake was probably buying into the whole Giuliani narrative and allowing a nongovernmental actor to interfere in a very ambiguous way with U.S. foreign policy.”

The working title of Sondland’s book is The Envoy: Mastering the Art of Diplomacy with Trump and the World. In it, he writes that he became a top diplomat because of “my relentless nature, my sometimes unhealthy drive and ambition, and a big serving of both candor and humor. It’s been a special formula of luck, pluck, and f---ing up that’s helped me achieve great success. It’s also created huge problems for me and those close to me.”

In addition to luck and pluck, Sondland also gave $1 million to Trump’s inaugural committee. Maybe he can recoup some of that money through book sales.