An attorney for Donald Trump threatened to sue the New York Times for defamation following publication of two women accusing Trump of sexual assault. The letter, written by Marc E. Kasowitz of the Manhattan firm Kasowitz, Benson, Torres & Friedman, can be seen above, and demands a retraction and apology and promising to “pursue all available actions and remedies” if these demands are unmet.

The Times published its response on social media:

With these dual lines drawn in the sand, it remains to be seen whether Trump will actually act on his threat to sue, but legal experts predict that The New York Times would defeat Trump in the action.

The New York Times also features in the Supreme Court case establishing the American definition of libel, New York Times v. Sullivan. In the 1964 case, the Court ruled that speech must be knowingly false or published with reckless disregard for the truth. In an email, Ken White, a litigator in Los Angeles and writer about free speech issues, characterizes the letter’s lack of substantive disputes of fact as “weak, but in a common and mundane way. Vagueness in legal threats is a hallmark of meritless thuggery, but you see it all the time. I do think that a failure to specify false statements means either they can’t or they are not doing so for tactical reasons that reflect badly on their case.”

The Times’s response hints that the second part of the definition also won’t work in Trump’s favor. “To prove malice, they’d have to prove that the NYT knew the information was false or showed reckless disregard about its falsity,” White says. “Reckless disregard doesn’t just mean sloppiness or failure to pursue every lead – it requires that the person be aware that the statement is probably false, or have serious doubts about its truth, and proceed anyway. That’s extremely hard to prove under normal circumstances. When it comes to someone like Trump who has bragged about exactly the sort of sexual assault he’s accused of, it will be especially hard.” The Times appears ready to defend against this allegation, noting the reporters “diligently worked to confirm the women’s accounts” and reached out to Trump for his response.

Journalist and Trump foe Megyn Kelly, who is an attorney, cast similar doubt on Twitter:

Risks: Defamation v. hard to prove since DT=pub figure. Also, truth is a defense so NYT will double down & will cast wide net in discovery. https://t.co/EQXohRafm4 — Megyn Kelly (@megynkelly) October 13, 2016

Trump has previously taken issue with this standard, wanting to “open up libel laws” to make suing the media easier. Trump’s critics accuse him of a pattern of SLAPP suits, or Strategic Lawsuits Against Public Participation, in which a plaintiff brings a suit against a defendant not out of a belief that it will prevail but in order to make the defendant withdraw criticism rather than withstand a lengthy and expensive trial. Several states have anti-SLAPP statutes wherein a defendant can file a pretrial motion to get a SLAPP thrown out immediately; however, White characterizes New York’s as “lousy” and unhelpful should the case be filed in New York, home state of both parties.

White also questions whether Trump would even want the potential damage involved with a trial, in light of rumored material that could hurt even worse if made public. “Tax returns are generally privileged from discovery. However, stuff like ‘bombshell recordings’ may be fair game, and Trump’s lawsuit might be a level to force The Apprentice producers to turn over raw footage despite confidentiality agreements. Discovery would be a bloodbath that would make the Red Wedding look like tea with your great-aunt,” White states.

It’s not the first time Trump has threatened legal action against his critics. Trump has either sued or threatened to sue journalists who questioned his wealth, a former contestant who criticized the Miss USA pageant, the organizer of a boycott aimed at getting Macy’s to stop carrying his products, and a rapper who used his name. Trump also claimed in September that he was holding his lawyers back from suing the Times for “irresponsible intent,” a phrase that does not exist in Constitutional law or jurisprudence: