Political speech, the Supreme Court has ruled, is at the apex of protected expression under the First Amendment — but what if that speech is intentionally deceptive about the time, place, or mechanics of voting?

That question is central to the case against Douglass Mackey, an Alt-Right Trump-supporting internet provocateur who posted to Twitter under the pseudonym “Ricky Vaughn” in the leadup to the 2016 election. Mackey was convicted in March of one count of Conspiracy Against Rights for posting two memes in the weeks before Election Day that encouraged Hillary Clinton supporters — specifically black and Latino ones — to vote by text message. He was sentenced in October to seven months in prison.

Mackey is out on bond pending his appeal with the United States Second Circuit Court of Appeals. He sat down with the Sun this week to discuss his case, which has become, according to the Harvard Law Review, “a lightning rod for legal spectators. And rightfully so.” Oral arguments begin April 5.

“I’m feeling very optimistic and very confident. The appeal is very strong,” Mackey tells the Sun. “This meme was clearly a parody. It’s clearly satire.”

More than 4,000 persons texted the number listed on the memes, one of which pictured a black woman with an “African Americans for Hillary” sign with the text “Avoid the Line. Vote from Home.” Mackey says he found the memes on 4chan and copied and pasted them to his feed. The image included a phone number and the Clinton campaign hashtags #ImWithHer and #GoHillary.

The vast majority of the texts to the meme number were made after several news outlets reported on the memes. Mackey says that some of the texts to the number said things like, “Hillary for prison,” and that the government failed to produce any witnesses who texted the number and then did not vote in person as a result.

The Harvard Law Review weighed in on Mackey’s appeal this month, concurring with Mackey that it “does indeed strain belief” to think Americans would be fooled by these memes. Mackey’s “Ricky Vaughn” Twitter profile picture was of Charlie Sheen with a red “Make America Great Again” hat. The memes were part of a Twitter feed filled with pro-Trump posts and often racist and antisemitic content. He was not hiding his political beliefs.

“While many would consider the speech in question to be repellent, the precedent created by Mackey is a dangerous one that lessens First Amendment protections in the digital marketplace of ideas,” the Harvard Law Review article says. “Using memes to prove a criminal conspiracy risks chilling a vast amount of speech on social media, especially if this is done without consideration of mens rea,” or criminal intent.

Mackey was convicted of violating a once-obscure Reconstruction-era law, 18 U.S.C. Section 241 — President Trump is now being prosecuted with the same charge for conduct related to January 6 — which was enacted in 1870 to prevent the Ku Klux Klan from conspiring to “injure, oppress, threaten, or intimidate” black Americans from exercising their constitutional rights, including the right to vote. Mackey’s case is the first time this law is being used to prosecute someone for deceptive speech, as opposed to conduct.

“Whatever one thinks of Mackey’s tweets, the district court’s broad reading of Section 241 brings the statute into conflict with the First Amendment and risks chilling protected political speech,” a law professor at UCLA, Eugene Volokh, writes in an amicus brief he submitted in support of Mackey’s appeal.  

“There are serious concerns that the statute is constitutionally vague,” the director of public advocacy at the Foundation for Individual Rights and Expression, Aaron Terr, tells the Sun. “That raises concerns that the government could also apply it to, say, allegedly false statements about political issues or political candidates that might have the effect of discouraging people from voting.”

“The First Amendment rightly prohibits prosecution of people simply for making false claims, so as to provide ample breathing room for public debate that’s essential to democracy,” Mr. Terr says.

Mackey’s attorneys argue that not only is Section 241 being interpreted in an overly broad way that infringes on First Amendment-protected political speech and satire, but that this is the first time the code is being used to prosecute merely deceptive speech on voting mechanics. Mackey, they say, did not have fair warning that his conduct was illegal. They are also appealing on venue grounds and that the government failed to prove the conspiracy requirement of Section 241.

“There’s no clearly established law saying this sort of speech, this sort of satire is illegal. So therefore there’s no fair notice,” Mackey says.  “If we’re going into these gray areas and prosecuting people for speech that is not clearly illegal, that can have a huge chilling effect on speech.”

Mackey tweeted the memes in 2016. He wasn’t arrested and charged until one month after President Biden’s inauguration in 2021. This raises questions about potential politicization at the Justice Department. A Hillary Clinton-supporting comedian, Kristina Wong, posted a satirical video to Twitter on Election Day 2016, in which she dons a red MAGA hat and urges her “fellow Chinese Americans for Trump” to vote on Wednesday, November 9, the day after the election. She was never charged.

Mackey’s arrest came four years after his posts and shortly after January 6, 2021, when the Democratic Party shifted its focus and messaging to “protecting democracy” and safeguarding voting. Mackey says he suspects his prosecution was politically motivated — the racist and antisemitic content on his pseudonymous account make him an unsympathetic character — but it is difficult to prove malicious or biased intent, so he did not include that in his appeal.

“There is no First Amendment right to spread knowingly false information about voting mechanisms and procedures in a federal election with the intent to disenfranchise voters,” another UCLA law professor and director of Safeguarding Democracy Project, Richard Hasen, writes in an amicus brief in support of the government. “Enforcement of this prohibition is particularly needed given the ease with which false information can be spread today by bad actors, and the growing loss of confidence in the integrity of our elections.”

Mr. Hasen declined to comment to the Sun. In a 2022 op-ed in the Times, Mr. Hasen mentioned Mackey’s case and urged Congress to pass a law barring deceptive speech about when, where, and how to vote. “A Trump supporter has been charged with targeting voters in 2016 with false messages suggesting that they could vote by text or social media post, but it is not clear if existing law makes such conduct illegal,” Mr. Hasen wrote.

Politics is a dirty game. Memes and online “shitposting” are the political pamphlets and cartoons of the digital age, Mackey says.

“It’s the rough and tumble politics that the Founders understood that they wanted to have, even if some stuff goes over the line,” Mackey says. “We don’t want the federal government to be the Oceania Ministry of Truth, you know from the whole Orwell books … this one’s a joke, this one’s serious, this was not a joke.”

Mackey says he has matured in the seven years since he posted under the name “Ricky Vaughn.” He was in his 20s then. He is now married with a family.

“There were absolutely offensive things that I said. … I’ve changed a lot,” Mackey says. Yet he says he doesn’t regret his conservative politics or supporting Mr. Trump, and he isn’t going to undergo “some sort of Bolshevik-style political reeducation.”

Despite the significant First Amendment arguments in Mackey’s appeal, the Second Circuit may reverse the district court’s conviction on improper venue. Mackey was tried in the Eastern District of New York, a liberal area encompassing Brooklyn and Queens, even though he lived in Manhattan in 2016 and none of his alleged conspirators lived in that district. The district court judge ruled that the venue was proper because Mackey’s tweets travelled through wires in the eastern district’s water and airspace.

Mackey’s attorneys argue this sets a dangerous precedent that internet-based crimes can be prosecuted in “any district that has an internet,” allowing prosecutors to pick and choose the most favorable to get a conviction. The internet is the new locus of political speech. The Harvard Law Review also raises concern about how 19^th century notions of conspiracy are being applied to 21^st century digital spaces and online satire.

When Vivek Ramaswamy was running for the GOP presidential nomination, he made pardoning Douglass Mackey “on Day One” a stump speech promise. Asked if he has spoken to Mr. Trump about a pardon, Mackey says he was a guest on Donald Trump Jr.’s podcast but otherwise has had no contact.

“I would like to try to win the appeal first to set the correct precedent for free speech in this country,” Mackey says. “If we don’t win at the Second Circuit, I absolutely would like to go to the Supreme Court.”

Mackey says that heading into a contentious 2024 election, with Mr. Trump ahead in the polls, Americans on both sides of the aisle are waking up to the threat of speech censorship and political prosecutions.

“If you’re going to drag people into court over stuff that’s satirical or even borderline satirical, or borderline parody, and charge them with conspiracy, where you don’t even have to prove that anyone was actually harmed, then it definitely cuts both ways,” Mackey says. “You don’t know what kind of regime will come into power and who they’re going to target.”