PANAMA CITY, Fla. — In November 2021, CNN ran a five-minute-long segment about private contractors who were charging large sums of money to evacuate Afghans desperate to flee the country in the wake of the American withdrawal.

“As CNN’s Alexander Marquardt has discovered, Afghans trying to get out of the country face a black market full of promises, demands of exorbitant fees, and no guarantee of safety or success,” anchor Jake Tapper said when introducing the piece.

The only security contractor mentioned by name in Marquardt’s report was Navy veteran Zachary Young, whose operation had been paid by several large companies — including Audible and Bloomberg LP — to extract dozens of Afghans. At one point in the segment, Young’s face was shown on-screen above a graphic referencing “black markets” and “exorbitant fees.”

Young sued CNN in June 2022, arguing that his business was destroyed by the segment, which he said falsely accused him of illegal activity and turned him into an “international pariah.”

After winding through Florida’s court system for the past 2½ years, the case is finally heading to trial in a Panama City courtroom starting Monday. CNN faces the potential of a sizable monetary judgment from a jury that could be predisposed against it, demographically, and at a time when public regard remains low for media outlets.

While most defamation lawsuits against media companies are either settled out of court or dismissed in their early stages, the Young case represents a rare example of a case actually going to trial, putting the network in the uncomfortable position of seeing its journalists, producers and executives being forced to take the stand.

To be able to win a large sum from CNN, Young’s team will have to prove that network staffers both intended to harm him and knew the segment was false or likely false and published it anyway. They will probably cite internal messages, obtained during the discovery process and made public in court motions, showing that some CNN staffers had spoken derogatively about Young, as well as messages in which staffers expressed reservations about the story, calling it “a mess,” “flawed,” “full of holes,” “incomplete” and “80% emotion, 20% observed fact.”

CNN has rejected Young’s allegations and argued that it had attempted to accurately report on Young’s business and was not referring to him when using the term “black market” to describe the ad hoc extraction market. (Although it argued in one motion that “no reasonable jury could find that the accusation that Young engaged in criminal activity is false.”)

CNN contends that its journalists believed what they were reporting about Young to be true, rebutting the legal standard known as actual malice, and even revealed private communications showing that one of the reporters who worked on the story viewed Young as “shady as hell” and an “a-hole” as proof. The CNN journalists, the network said, were “legitimately disgusted at what their research revealed about his conduct.”

And after Young sought a retraction, CNN issued an on-air apology and a “correction,” noting that the story “did not intend to suggest that Mr. Young participated in a black market.”

“When all the facts come to light, we are confident we will have a verdict in our favor,” a CNN spokesperson told The Washington Post ahead of this week’s trial.

The network suffered a setback when Florida Circuit Judge William S. Henry, who is overseeing the case, ruled this past fall that Young’s activities were legal, preventing the network from suggesting to jurors that he may have been engaging in illicit behavior. If the jury determines the term “black market” to refer to illegal activity, CNN could be found to have knowingly published false information, as network journalists acknowledged their reporting did not find evidence that Young committed a crime.

The case has been particularly contentious. Last month, CNN protested to Henry, who was appointed by Florida Gov. Ron DeSantis (R) in 2020, that Young’s lawyers had improperly grilled Tapper in a sworn deposition about topics that were not permitted, including his thoughts about President-elect Donald Trump and Fox News’s decision to settle a defamation lawsuit filed by Dominion Voting Systems.

Aimee Edmondson, a professor of media law and journalism history at Ohio University, said that internal messages expressing doubt about the story could hurt CNN at trial — though she said the case is “not a slam dunk.”

“It looks to me like there was enough concern internally that that story wasn’t quite cooked yet, so maybe they needed to take a little bit more time and find a bit more sourcing and maybe reconsider some of their word choices,” she said. “The argument that it’s sloppy and tabloid-like, from where I sit, not being involved in the case, is a pretty good argument. Is that actual malice? It’s going to be for the jury to say.”

Media companies such as ABC News, Fox News, Newsmax and One America News have all recently chosen to settle cases rather than open up their internal processes to the scrutiny of a jury. The fact that CNN has not is notable to legal observers.

“Very few media defendants want to face juries these days,” said David A. Logan, professor emeritus at the Roger Williams School of Law.

The first step in the case on Monday is picking a panel of jurors, a process that is particularly crucial for CNN, considering the demographics of the potential panel.

In November, about 73 percent of Bay County, where the trial will be held, voted for Trump in the presidential election. Because Trump supporters largely view CNN unfavorably, jurors could treat the network’s arguments skeptically. The county is also home to several military bases — another advantage for Young, a veteran.

“You can hardly imagine this case being in a worse place for CNN given this plaintiff, this allegation and this likely jury pool,” Logan said.

Legal observers considered the possibility of an unfavorable Florida jury as a possible reason ABC last month chose to settle Trump’s defamation lawsuit against the network, potentially fearing a large award in the president-elect’s favor. In 2016, a Florida jury did just that, awarding the former wrestler Hulk Hogan $115 million in an invasion of privacy case that bankrupted Gawker Media.

Although many press advocates view defamation cases as an incursion on fundamental First Amendment freedoms, Edmondson said the Young trial could inadvertently serve as a primer for the public on how media companies work to ensure that their reporting is accurate.

“It’s a great chance to explain the newsgathering process and how we do what we do, and I really think CNN should lean into that,” Edmondson said. “This is an opportunity to educate the public, and we don’t really take advantage of that enough.”