Before becoming President Donald Trump’s ambassador to Germany and acting director of national intelligence, Richard “Ric” Grenell had a bare-knuckled career in public relations.

The Republican operative served as spokesman at the United Nations during the George W. Bush administration and then moved to Capitol Media Partners, a firm that represented a host of clients. Grenell’s work in private practice for foreign clients has drawn scrutiny, particularly work for a Moldovan oligarch and a nonprofit funded largely by a far-right Hungarian political party.

In his telling, he has also advised two of Hollywood’s biggest celebrities: actors George Clooney and Ryan Gosling. A 2016 Los Angeles Business Journal story, based on an interview with the future ambassador, reported that he had worked with the two stars. “Grenell has advised Hollywood celebrities such as Ryan Gosling and George Clooney – but only on ‘substantive issues’ never ‘fluff,’” read the piece.

And Grenell’s personal website—now archived—also touted work with the leading men.

“Grenell has consistently worked with leaders in Washington, D.C. and in Hollywood to support issues as diverse as kidney disease and the war in Sudan, utilizing celebrities such as George Clooney, Ryan Gosling, Sophie B. Hawkins, and Alonzo Mourning, to name a few,” the site said.

Representatives of Gosling did not respond to requests for comment. A Clooney rep, meanwhile, contradicted Grenell’s description of events.

“I saw where he was quoted as saying that but George never solicited nor received advice from him,” the rep wrote in an email, adding that it’s possible the two men met in Sudan but that Clooney has no recollection of it.

Grenell told The Daily Beast in an email that through his work as a spokesperson at the U.N., he regularly encountered celebrities advocating on human rights issues.

“I spent 8 years at the UN where Darfur, the larger issue of Sudan/South Sudan and other humanitarian issues were regularly discussed inside the Security Council and other Committees with celebrities like Clooney, Gosling and many others who came as UN Ambassadors to learn more and lobby for more,” he wrote. “My team and I regularly gave these celebrities our advice about US funding priorities and suggestions of how to appeal for more funds to combat the problems they were highlighting.”

Grenell’s most notable celebrity work likely came in the private sector, when he represented telenovela star Kate del Castillo, according to the Los Angeles Business Journal. He worked for her after she held a meeting with actor Sean Penn and drug cartel chief Joaquín “El Chapo” Guzmán. Guzmán, a fan of the telenovela del Castillo starred in called La Reina del Sur, reached out to her through his lawyers about a possible movie deal, according to the Los Angeles Times. There were later reports that the meeting helped law enforcement track down the cartel boss and arrest him. He was extradited to the U.S. and is serving a life sentence.

The situation created a bit of a P.R. problem for del Castillo, to put it lightly. Mexican authorities investigated her for money laundering, according to the Los Angeles Times, and she had to leave the U.S. for nearly three years. Grenell told the Los Angeles Business Journal that he helped the actress handle the crisis. The publication reported that his plans “would involve an extensive diplomacy campaign.”

A rep for del Castillo declined to comment, and Grenell did not elaborate on his work for the soap star. But his diplomatic efforts appear to have succeeded; the actress was never charged with any crimes, and she starred in a second season of the telenovela that caught Guzmán’s eye.

Grenell, meanwhile, has ascended to the highest levels of the Trump administration. Last week, the president abruptly fired acting Director of National Intelligence Joseph Maguire and gave his post to Grenell—making him the first openly LGBTQ person to hold a Cabinet-level position in the United States government. He is maintaining his role as ambassador to Germany and worked from Berlin to push back against Russian efforts to deepen its energy ties to Germany, including vocal opposition of the Nord Stream 2 pipeline project. Trump signed legislation sanctioning the project late last year.

Grenell’s move to the Office of the Director of National Intelligence has also raised concerns about political interference in intelligence-gathering, given his background as a Republican political operative and lack of any experience working for an intelligence agency.