A Trump-supporting internet trickster who tried to fool supporters of Hillary Clinton into not voting in 2016 was slapped this week with a seven-month prison term. The case raises new questions whether the government should prosecute internet trolls and others  online who intentionally spread false information about voting. Will  doing so stifle political debate or constitutionally protected speech?

Those questions are central to the case against Douglass Mackey, a Donald Trump-supporting internet troll who, during the 2016 election, posted on Twitter, now called X, under the pseudonym “Ricky Vaughn.” Mackey, 33, was convicted in March and sentenced Tuesday to seven months in prison for “attempting to deprive individuals from exercising their sacred right to vote for the candidate of their choice.”

Mackey did that, according to the Justice Department, by encouraging Hillary Clinton voters to skip the polls and vote by text — an impossibility.

The conviction and  jail sentence could have a “chilling effect” on political speech, particularly online, as America heads into the 2024 election, the director of public advocacy at the Foundation for Individual Rights and Expression, Aaron Terr, tells the Sun. He adds that the case also raises concerns about “selective enforcement” — in this case, selective enforcement targeting a Trump supporter who sought the downfall of Ms. Clinton.  

In the leadup to the 2016 election, Mackey posted pro-Trump memes and right wing, often-inflammatory commentary to his 58,000 Twitter followers. His “Ricky Vaughn” account, which featured a profile picture of Charlie Sheen in a red MAGA hat, was more influential in 2016 election politics than NBC News, CBS News, and Stephen Colbert, according to a 2016 analysis by the MIT Media Lab.

Prosecutors in the United States District Court for the Eastern District of New York say that Mackey used his social media reach and “conspired” with other online influencers to “limit Black turnout” with a fraudulent text-to-vote scheme and a “coordinated disinformation campaign” aimed at  helping to throw the election to Mr. Trump.

The main evidence is a meme, which Mackey posted just days before the 2016 election, of a Black woman in front of an “African Americans for Hillary” sign with the text “Avoid the Line. Vote from Home.” The image also says “Text ‘Hillary’ to 59925,” and in the fine print below, “Must be 18 or older to vote. One vote per person.” The post included the Clinton campaign hashtags #ImWithHer and #GoHillary.

Federal prosecutors say that at least 4,900 unique telephone numbers texted the number in the meme, despite the fact that Mackey’s profile picture had a MAGA hat and that a simple Google search would make it clear that it was impossible to vote by text. 

Federal prosecutors turned to an obscure 1870 law, which was designed to prevent the Ku Klux Klan from impeding or intimidating Black Americans from voting during Reconstruction, to prosecute Mackey.

“The conviction definitely raises First Amendment concerns,” Mr. Terr tells the Sun. “The First Amendment generally protects even false speech because we don’t want the government prosecuting people for satire or hyperbole or targeting dissenting speech under the guise of combating misinformation.”

Mr. Terr says the 1870 statute used in this case is “vaguely worded,” and the concern is that “this case doesn’t make it clear how far the government will be willing to go in prosecuting what it considers false information under this statute.”

“It raises concerns that the government could also apply it to saying allegedly false statements about political issues or political candidates that might have the effect of discouraging people from voting,” Mr. Terr says.

What if a person posts to X or Facebook that both the Republican and Democratic candidates in 2024 are unworthy and encourages people to stay home in protest instead of voting? What if a person falsely posts that the voting line is four hours long, thereby discouraging people from going to the polls? What about satire? As we’ve seen with government involvement in censoring Covid “misinformation” online, putting the government in charge of setting speech parameters is problematic.  

Mackey’s attorney argued that his client’s posts were constitutionally protected speech, but the judge was not persuaded. Mackey faced up to ten years in jail, so the seven-month sentence is far lighter than it could have been. Yet many free speech advocates are crying foul that he was prosecuted at all.

“It is a flagrant violation of Mackey’s First Amendment rights,” GOP presidential candidate, Vivek Ramaswamy, tells the Sun.

Mr. Ramaswamy and others are pointing to the actions of comedian and Hillary Clinton supporter, Kristina Wong, who posted to Twitter in the leadup to the 2016 election a video in which she claimed to be a Trump supporter and advised viewers to make sure to vote on November 9, the day after Election Day. “I just want to remind all my Chinese Americans for Trump, people of color for Trump — vote for Trump on November 9^th,” she urged her viewers.

Ms. Wong’s post is still up on X. She was never prosecuted for trying to trick people of color into not voting.

Mr. Ramaswamy says Mackey’s trial was a “political prosecution.” He is promising to pardon him if elected president. “I won’t wait until the last day like presidents usually do,” Mr. Ramaswamy says. “I’ll get it done on January 20, 2025 and take the backlash if I have to.”

Mackey’s posts may have been offensive— but so are neo-Nazis marching at Skokie or pro-Hamas protests on college campuses today. There’s a reason we protect free speech at the margins — and today, even anodyne political speech is often offensive to one segment of the population.

“If we’re going to make an exception” to free speech, Mr. Terr says, “then we better be damn careful about ensuring that exception is really narrow, and only involves existing exceptions like fraud, defamation, and doesn’t just capture a wide range of political speech, or even unintentionally false claims.”