Fox News senior judicial analyst Judge Andrew Napolitano on Wednesday helpfully explained to Fox host Charles Payne that the $250 million lawsuit against the Washington Post filed by the family of Covington Catholic student Nick Sandmann faces a tough road, adding that it is “impossible” to prove that level of damages claimed.

Noting that President Trump gave his support to Sandmann’s suit, which contends the Post targeted and bullied the MAGA hat-wearing teenager in an effort to embarrass the president, Payne asked Napolitano if Sandmann, 16, has a case.

The judge weighed both sides of the argument, claiming the teen “probably suffered” as a result of “false and erroneous” portrayals of his interactions last month with a Native American activist. On the other side, Napolitano pointed out, the student became a “limited purpose public figure” during the confrontation, adding that Sandmann’s lawyers would need to then prove the Post “published what they knew was false and reckless.”

Arguing that legal guidelines state that a minor doesn’t have a reputation to defame, Napolitano added that even if the lawyers were able to find the Post was reckless, there wouldn't be a way to prove the damage to the teen’s reputation.

“Other lawyers know that you can’t demand a number in court unless you can actually prove that,” he said. “And I suggest to you, it’s impossible to prove damages for a 16-year-old to reputation of $250 million.”

Payne countered that numerous celebrities “wrecked” Sandmann and that it seemed obvious that the teenager was impacted for the rest of his life, causing Napolitano to explain that lawyers would have to directly tie the Washington Post directly to that.

“You can make fair comment,” Napolitano observed. “We start from the proposition that the freedom of speech is protected and defamation is an exception, a very narrow exception. When it’s a public event, the exception is even narrower.”

An exasperated Payne wanted to know if there was “any onus” on the Post to be held responsible in an environment where “anything involving a red hat creates a villain out of the person wearing the red hat.”

Napolitano concluded by telling the Fox host that while he makes a “very strong moral case,” the law “does not impose a moral standard on the Washington Post to engage in restraint.”