Grenell became one of many Fox News personalities who joined the Trump administration when he was confirmed as ambassador to Germany in 2018.

He is also an avowed fan of the far-right Breitbart news site. “It’s no joke that I’m a Breitbart fan, and I read it every day,” he told them in a 2018 interview. “They ‘got me’ early on, and what I mean by that is Breitbart sees the value of a consistent conservative, and you have a lot of choices in getting your message out. For me, it hasn’t always been perfectly positive coverage, and sometimes they report on things I don’t feel comfortable with, but that is the beauty of it. I love the courageousness of it. I hope I’m just as courageous.”

He had previously served as spokesperson for the U.S. delegation to the United Nations during the George W. Bush years — during which time his duties included voicing the administration’s support for the Iraq War. In 2012, he was forced to resign from his position as a foreign policy and national security spokesperson for the Mitt Romney campaign after key right-wing religious figures objected to Romney hiring a gay man.

Over the years, Grenell also gained a reputation for denigrating prominent women on both sides of the aisle online, including Hillary Clinton, MSNBC host Rachel Maddow, and U.S. ambassador to the Holy See Callista Gingrich, the wife of former Speaker of the House Newt Gingrich.

As an example of his prolific online trolling, Grenell once took an unremarkably inclusive tweet from Hillary Clinton, recognizing the Easter holiday, and accused her of being “nervous about offending Muslims."