The news conference was beaming live across the nation. The country's leader was hunched over a podium before reporters. CNN's Jim Acosta gripped a microphone and fired off a tough question.
"Why do you have Cuban political prisoners?" Acosta asked. "And why don't you release them?"
It was March 2016 in Havana. Then-President Barack Obama and Cuban President Raúl Castro were holding a joint news conference to mark the American president's historic visit to the island nation. Castro, the longtime, strongman head of an oppressive regime infamous for squashing dissent and muzzling the press, was clearly uncomfortable fielding questions from a journalist. As the New York Times reported at the time, it was a first time a foreign reporter had addressed Cuban leadership since the 1950s.
But handlers did not swoop in to grab Acosta's microphone. The reporter - whose own father was a Cuban exile - was not hauled out of the room. His credentials were not tossed. Instead, the Cuban leader grumbled out a non-answer. "Give me a list of the political prisoners and I will release them immediately," Castro said.
Fast-forward two years, and Acosta had a very different experience Wednesday tangling with presidential power on-air.
Following the mixed-results of this week's midterm elections, President Donald Trump held a news conference that quickly descended into a full-contact grudge match against Democrats, failed Republicans candidates and the press.
"CNN should be ashamed of itself having you working for them," Trump thundered to Acosta after the reporter asked a question about the president's inflammatory rhetoric on immigration. "You are a rude, terrible person. You shouldn't be working for CNN."
Hours later, Acosta announced the White House had suspended his press credentials. In a statement, White House press secretary Sarah Sanders said Acosta had lost his hard pass after "placing his hands on a young woman" who was trying to take away the reporter's microphone during his testy back-and-forth with Trump.
"This is a lie," Acosta stated on Twitter, later explaining to CNN's Anderson Cooper that the White House was "trying to shut us down. I think they're trying to send a message to my colleagues."
Acosta's yanked credentials have created a firestorm in media circles - and pulled much of the press focus off the midterm results and the abrupt dismissal of Attorney General Jeff Sessions. It's also the latest cycle in the reporter's complicated relationship with administration. Depending on your political stripes, the move was either a dangerous attack on the First Amendment, or a showboating reporter's comeuppance.
Since 2016, Acosta has become one of the press corps' most high-profile members, regularly sparring with administration officials, such as Sanders and White House adviser Stephen Miller. For Trump - who repeatedly vents his anger at the press and CNN in particular - Acosta is a convenient foil. But the reporter's bulldog reporting style has made him a household name.
"I probably receive more death threats than I can count," Acosta told Variety this year. "I get them basically once a week."
If there's a precursor to Acosta's style in the White House media landscape, it was Sam Donaldson. During the latter part of the Reagan administration, the president would go months between taking questions from the press. The ABC White House correspondent began lobbing questions at President Ronald Reagan during public appearances.
"Donaldson has been both praised and panned for his aggressive reporting on a distanced President, for shouting questions at Reagan in a megaphone voice that can be heard even above the helicopter rotors when the Reagans take off for Camp David," the Christian Science Monitor wrote in 1987.
Acosta, who grew up in Washington, D.C., area and graduated from James Madison University, first landed at CNN in 2007 after a number of years working for local and network television stations. For the network, he began covering political stories, including Mitt Romney's 2012 presidential campaign and the Obama White House, according to a Politico profile published last year.
The reporter's first memorable on-air brush with Trump set the stage for much of their later relationship. In May 2016, Acosta asked them candidate about media attention.
"I've watched you on television," Trump responded. "You're a real beauty."
Acosta has not wilted when faced with Trump's jeremiads against his press coverage. Rather, like his encounter with Castro, he doubles down by challenging Trump's statements in on-air confrontations that are packed with tension and barely buried anger - TV-ready exchanges that perfectly encapsulate the president's fraught relationship with the press. "When the president of the United States calls the press 'fake news' and 'the enemy of the American people,' . . . I think that's when you have to get tough and ask the hard questions," Acosta told The Washington Post in 2017.
A perfect example arrived just days before Trump's inauguration in January 2017, when the reporter and president-elect sparred over the allegations contained in the infamous Steele dossier published by BuzzFeed.
"Not you. Your organization is terrible," Trump said to Acosta, as the reporter attempted to ask a question.
"Since you're attacking us, can you give us a question? Mr. President-elect, since you're attacking our news organization, can you give us a chance?" the reporter replied.
"I'm not going to give you a question," Trump shot back. "You are fake news."
Since then, Acosta has regularly sparred with Trump. Following the violent "Unite the Right" hate rally in Charlottesville, Va., last year, Acosta checked Trump when the president asserted there were "some very fine people on both sides."
"No, sir, there are no fine people in the Nazis," Acosta retorted.
The reporter similarly lobbed pointed questions at Trump during the president's summit with North Korean leader Kim Jong Un in June. The exchange led Trump's 2020 campaign manager Brad Parscale to call for Acosta to "immediately have his press credentials suspended."
Acosta tapped out a quick retort on Twitter.
"Dear Brad," he wrote. "[D]ictatorships take away press credentials. Not democracies."