Nicholas Sandmann, the high school student at the center of the viral Lincoln Memorial confrontation in January, wants to “punish” CNN and the Washington Post for attempting to “assassinate” his character. He wants to teach the Post “a lesson it will never forget” and halt CNN’s “biased agenda against President Trump” and his supporters. In the process, Sandmann wishes to collect more than a half-billion dollars from the two outlets. The media targeted him because he was a “white, Catholic student who was wearing a MAGA cap,” Sandmann believes. Only $525 million in damages will fully compensate him and deter these “bullies” from “again bullying other children.”

This argument, laid out in Sandmann’s two lawsuits against CNN (filed on Tuesday) and the Washington Post (filed in February), is one part legal theory, two parts political screed. Sandmann’s lawyer, famed libel attorney L. Lin Wood, knows that these suits are a long shot: The First Amendment protects the press’ right to report on a national controversy without a full grasp on the facts, and to provide commentary that ultimately proves inaccurate. Wood’s defamation lawsuits are designed to scare CNN and the Post, to chill their future criticisms of “individuals perceived to be supporters of the President.” His crusade is just another skirmish in President Donald Trump’s attack on “fake news.”

Like most mainstream media outlets, CNN and the Washington Post provided an incomplete and unduly harsh description of the January encounter between Sandmann and Nathan Phillips, a Native American activist. On the basis of a viral Twitter video, reporters at these companies alleged that Sandmann, a 16-year-old March for Life participant wearing a MAGA hat, attempted to “harass,” “accost,” or “mock” Phillips. Commentators on CNN condemned Sandmann as racist and aggressive toward Phillips. Articles in the Post alleged that he threatened and intimidated the activist.

It is safe to say that neither CNN nor the Post covered themselves in glory.

Within days, other videos of the event provided a more complete and nuanced picture of the encounter. Before Phillips arrived, Sandmann and his classmates from Covington Catholic High School had been taunted by the Black Hebrew Israelites, a notorious cult that hurls bigoted slurs at passers-by in Washington. These students say that they performed school spirit chants to counter the (indisputably vile) verbal assault. Phillips and his associates say they interpreted these chants as racist toward their nearby Indigenous Peoples March, which had concluded earlier in the day. He approached the students, beating a drum and singing a tribal song. At least one student—though not Sandmann—then made the “tomahawk chop,” an offensive gesture, and several wore MAGA apparel as they stood in front of Phillips. After about two minutes, the Covington Catholic students retreated to their bus.

How do you interpret this incident? Reason’s Robby Soave, one of the first media figures to rebuke the developing narrative of Sandmann’s alleged aggression, believes he and his friends did essentially nothing wrong. Talking Points Memo’s Josh Marshall, by contrast, wrote that the longer video “doesn’t greatly change the substance” of the widespread first impression—that a “bemused and cocky teenager,” Sandmann, faced off with a “Native American activist/elder,” Phillips, while his classmates “jeer and taunt the man with chopping motions.” Vox’s Zack Beauchamp asserted that “it’s impossible to know with certainty who has a more accurate read of the situation.”

It is safe to say that neither CNN nor the Post covered themselves in glory by credulously painting Sandmann as the obvious aggressor on the basis of a brief video edited to convey precisely that perception. And no teenager deserves the campaign of fury, including death threats, that greeted Sandmann. It is perfectly appropriate to criticize the media for reporting the encounter without a full set of facts, which—viewed most favorably to Sandmann—absolve him of his critics’ worst charges.

That, however, is not what Wood has chosen to do. Instead, in a promotional video put out by his firm, Wood accuses the media of engaging in a coordinated assault on Sandmann’s character as part of a campaign to vilify Trump and destroy the country. As images of anti-Trump protests and riots flash across the screen, a narrator declares:

The Washington Post, owned by the richest man in the world, led the false attacks on Nicholas’ reputation. CNN led the broadcast media’s charge against Nicholas. Both recklessly spread lies about a minor to advance their own financial and political agendas. How long will we allow these media giants to tear at the fabric of our lives to further their own agendas? Will they ever be held accountable?

This inflammatory rhetoric is drawn largely from the lawsuits themselves. The suit against the Post berates Jeff Bezos by name and demands $250 million in damages seemingly because that’s how much he “paid in cash for the Post.” It denounces the paper for ignoring “basic journalist standards because it wanted to advance its well-known and easily documented, biased agenda against President Donald J. Trump.” (Trump tweeted this quote and wrote: “Go get them Nick. Fake News!”) CNN gets similar treatment: “From at least as early as the November 2016 election of Donald J. Trump as the 45th President of the United States,” the lawsuit states, “CNN has maintained a well-known and easily documented biased agenda against President Trump.” Apparently in support of this claim, the suit notes that “President Trump publicly and repeatedly branded CNN as the poster child of ‘fake news.’ ”

All of this may satisfy the president, but it likely won’t satisfy the courts. Wood insists that Sandmann is not a public figure, which would allow him to sue the media for mere negligence—a failure to take reasonable care to avoid unjustly injuring his reputation. It is debatable whether the Post and CNN even met that low bar: Drawing conclusions from a video rocketing around the internet is not clearly unreasonable when those conclusions later prove questionable in light of new evidence.

Regardless, Sandmann probably qualifies as a “limited-purpose” public figure, which means he must prove more than mere negligence to win his defamation lawsuits. Sandmann played a starring role in a story that drew widespread attention, then sought to shape the narrative by appearing on a major news program. His engagement in this public debate thrust him into the spotlight, and even if his participation was initially involuntary, he may still qualify as a public figure for First Amendment purposes. The courts have acknowledged that an individual may become a public figure “through no purposeful action of his own” when he plays a “central, albeit involuntary, role in [a] controversy.” To win his suit, then, Sandmann should have to prove not just negligence but “actual malice,” demonstrating that CNN and the Post acted with “reckless disregard” for the truth, or knowledge of their alleged lies.

It is difficult to see how Sandmann could clear this high bar. Journalists continue to debate just how badly the media botched its immediate coverage of the encounter. Even fierce critics of this coverage, like Soave, question whether outlets acted with “actual malice” or just rashly. The media will always jump on a story consuming the public and draw conclusions that might not withstand close scrutiny down the road. Even when reporters get the story wrong, the First Amendment may still protect their right to speak.

There is still a slim but real possibility that Sandmann will persuade the courts that the Constitution does not shield CNN and the Post from his lawsuit. He may then convince a jury to slap both outlets with crippling damages. If so, expect a court to substantially lower those damages, since Sandmann cannot possibly prove that $525 million is an appropriate award. If the student wins, Trump will declare victory, and Sandmann’s fiercest defenders will feel vindicated. The press, meanwhile, may hesitate before jumping into the next public debate spurred by a seemingly outrageous video. Whether you think that’s a threat to free expression or a necessary safeguard against bias will probably depend on how you feel about Nicholas Sandmann.