For years at CNN, Don Lemon had been a thorn in the side of President Trump, frequently taking him to task during his first term over his comments about immigrants and other matters.

On Friday, the former CNN anchor — now an independent journalist who hosts his own YouTube show — was in a federal courtroom in Los Angeles and charged with conspiracy and interfering with the 1st Amendment rights of worshipers during the Jan. 18 protest at the Cities Church in St. Paul, Minn.

Lemon was arrested by federal agents in Los Angeles on Friday, along with a second journalist and two of the participants in the protest of the U.S. government’s immigration enforcement tactics in Minneapolis.

Lemon identified himself at the protest as a journalist. His attorney said in a statement Lemon’s work was “constitutionally protected.”

“I have spent my entire career covering the news,” Lemon told reporters after he was released on his own recognizance Friday afternoon. “I will not stop now. There is no more important time than right now, this very moment, for a free and independent media that shines a light on the truth and holds those in power accountable. Again, I will not stop now. I will not stop, ever.”

The scene of a reporter standing before a judge and facing federal charges for doing his job once seemed unimaginable in the U.S.

The arrest marked an extraordinary escalation in the Trump administration’s frayed relations with the news media and journalists.

Earlier this month, the FBI seized the devices of Washington Post reporter Hannah Natanson in a pre-dawn raid as part of an investigation into a contractor who has been charged with sharing classified information. Such a seizure is a very rare occurrence in the U.S.

Last spring, the Associated Press was banned from the White House. The AP sued White House Press Secretary Karoline Leavitt and two other administration officials, demanding reinstatement.

Even the Committee to Protect Journalists, an organization that monitors and honors reporters imprisoned by authoritarian government regimes overseas, felt compelled to weigh in on Lemon’s arrest.

“As an international organization, we know that the treatment of journalists is a leading indicator of the condition of a country’s democracy,” CPJ Chief Executive Jodie Ginsberg said in a statement. “These arrests are just the latest in a string of egregious and escalating threats to the press in the United States — and an attack on people’s right to know.”

For Lemon, 59, it’s another chapter in a career that has undergone a major reinvention in the last 10 years, largely due to his harsh takes on Trump and the boundary-pushing moves of his administration. His journey has been fraught, occasionally making him the center of the stories he covers.

“He has a finely honed sense of what people are talking about and where the action is, and he heads straight for it in a good way,” said Jonathan Wald, a veteran TV producer who has worked with Lemon over the years.

A Louisiana native, Lemon began his career in local TV news, working at the Fox-owned station in New York and then NBC’s WMAQ in Chicago, where he got into trouble with management. Robert Feder, a longtime media columnist in Chicago, recalled how Lemon was suspended by his station for refusing to cover a crime story that he felt was beneath him.

“A memorable headline from that era was ‘Lemon in Hot Water,’” Feder said.

But Lemon’s good looks and smooth delivery helped him move to CNN in 2006, where his work was not always well-received. He took over the prime time program “CNN Tonight” in 2014 and became part of the network’s almost obsessive coverage of the missing Malaysia Airlines Flight 370. (Lemon was ridiculed for asking an aviation analyst if the plane might have been sucked into a black hole.)

Like a number of other TV journalists, Lemon found his voice after Trump’s ascension to the White House. He injected more commentary into “CNN Tonight,” calling Trump a racist after the president made a remark in the Oval Office about immigrants coming from “shithole countries” to the U.S.

After George Floyd was murdered by a police officer in Minneapolis in May 2020, Lemon’s status as the lone Black prime time anchor on cable news made his program a gathering place for the national discussion about race. His ratings surged, giving CNN its largest 10 p.m. audience in history with 2.4 million viewers that month.

Lemon’s candid talk about race relations and criticism of Trump made him a target of the president’s social media missives. In a 2020 interview, Lemon told The Times that he had to learn to live with threats on his life from Trump supporters.

“It’s garnered me a lot of enemies,” he said. “A lot of them in person as well. I have to watch my back over it.”

Lemon never let up, but CNN management had other ideas. After Warner Bros. Discovery took control of CNN in 2022, Chief Executive David Zaslav said the network had moved too far to the political left in its coverage and called for more representation of conservative voices.

Following the takeover, Lemon was moved out of prime time and onto a new morning program — a format where CNN has never been successful over its four-decade-plus history.

Lemon’s “CNN Tonight” program was built around his scripted commentaries and like-minded guests. Delivering off-the-cuff banter in reaction to news of the moment — a requirement for morning TV news — was not his strong suit.

Lemon had a poor relationship with his co-anchors Poppy Harlow and Kaitlan Collins. The tensions came to a head in February 2023 after an ill-advised remark he made about Republican Nikki Haley, who had been running for president.

Lemon attempted to critique Haley’s statements that political leaders over the age of 75 should undergo competency testing.

“All the talk about age makes me uncomfortable — I think it’s a wrong road to go down,” Lemon began. “She says politicians, or something, are not in their prime. Nikki Haley isn’t in her prime — sorry — when a woman is considered to be in her prime in her 20s and 30s, maybe 40s.”

Harlow quickly interjected, repeatedly asking Lemon a couple of times, “Prime for what?” Lemon told his female co-anchors to “Google it.” It was one of several sexist remarks he made on the program.

Lemon was pulled from the air and forced to apologize to colleagues, some of whom had called for his dismissal. He was fired in April 2023 on the same day Fox News removed Tucker Carlson.

Lemon was paid out his lucrative CNN contract and went on to become one of the first traditional TV journalists to go independent and produce his own program for distribution on social media platforms.

“Others might have cowered or taken time to regroup and figure out what they should do,” said Wald. “He had little choice but to toil ahead.”

Lemon first signed with X in 2024 to distribute his program as the platform made a push into longer-form video. The business relationship ended shortly after new X owner Elon Musk sat down for an interview with Lemon.

Musk agreed to the high-profile chat with no restrictions, but was unhappy with the line of questioning. “His approach was basically ‘CNN but on social media,’ which doesn’t work, as evidenced by the fact that CNN is dying,” Musk wrote.

An unfazed Lemon forged ahead and made his daily program available on YouTube, where it has 1.3 million subscribers, and other platforms. He has a small staff that handles production and online audience engagement. In addition to ad revenue from YouTube, the program has signed its own sponsors.

While legacy media outlets have become more conscious of running afoul of Trump, who has threatened the broadcast TV licenses of networks that make him unhappy with their coverage, independent journalists such as Lemon and his former CNN colleague Jim Acosta have doubled down in their aggressive analyses of the administration.

Friends describe Lemon as relentless, channeling every attempt to hold him back into motivation to push harder. “You tell him ‘you can’t do it,’ he just wants to do it more,” said one close associate.

Wald said independent conservative journalists should be wary of Lemon’s arrest.

“If I’m a conservative blogger, influencer, or YouTube creator type, I would be worried that when the administration changes, they can be next,” Wald said. “So people should be careful what they wish for here.”