Social media platforms have become the arena of choice for sarcastic, cruel, and often mean-spirited political discourse. During the 2016 election, this was particularly true of Twitter,1 where groups of warring internet personalities sought to one-up each other by posting biting political memes with the hope of influencing voters.2 Some commentators have cited these posters as a major force in the rise of President Donald Trump;3 Hillary Clinton famously decried them as "deplorables."4 One such deplorable was Ricky Vaughn, a pro-Trump far-right figure who posted hundreds of thousands of tweets during the 2016 election, many of which were supportive of then-candidate Trump.5 Seven years later, the man behind the account would be found guilty of conspiring to injure the rights of voters for posting two memes that falsely claimed voters could submit their vote by text. Recently, in United States v. Mackey, 6 the indictment and subsequent conviction of one of 2016's most famous internet trolls has become a lightning rod for legal spectators.7 And rightfully so. 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.During the lead-up to the 2016 presidential election, Douglass Mackey, also known as "Ricky Vaughn"8 on social media, was a prolific figure in the alt-right,9 a loose online movement associated with the rise of then-candidate Donald Trump.10 Ricky Vaughn's account had a Twitter audience of some 58,000 followers, and Vaughn was ranked by MIT Media Lab as one of the most important influencers of the upcoming election, ahead of figures like comedian Stephen Colbert.11 Mackey's oeuvre included far-right-wing memes and incendiary comments often aimed at figures Mackey derided as "shitlibs."12 Described as an "indefatigable circulator of edgy memes and rah-rah Donald Trump boosterism," Mackey's account was ultimately banned in October 2016. 13 After the election, Mackey faded into obscurity for several years14 until he was charged by the U.S. Department of Justice in January 2021, 15 days after President Biden took office. The complaint against Mackey was filed in the U.S. District Court for the Eastern District of New York.16 It accused Mackey of engaging in a conspiracy to deprive people of their rights (here, the right to vote) by intentionally making false statements with the aim of tricking Clinton supporters into "voting" by text instead of casting their ballots at the polls.17 This would violate 18 U.S.C. 241, 18 a latter-day codification of the Enforcement Act of 1870, 19 which prohibits individuals from engaging in a conspiracy against voting rights. The complaint centered on Mackey's alleged posting of two memes in November 2016 that encouraged potential voters to "Avoid the [Voting] Line" and vote for Hillary Clinton by texting a fictitious number.20 According to text message records, some 4,900 unique telephone numbers texted the fictitious number,21 possibly instead of casting their legitimate ballots in person. To establish a conspiracy, the complaint included online conversations Mackey allegedly took part in with four coconspirators.22 Mackey was indicted in February 2021 and charged with a single count of violating 18 U.S.C. 241. 23 Mackey filed a motion to dismiss,24 claiming that venue was improper,25 that the indictment violated his due process rights,26 and that, even if 241 applied to the tweeted memes, its use to convict Mackey would unconstitutionally interfere with his First Amendment rights.27 His primary First Amendment assertion revolved around an interpretation of Mackey's speech as political in nature28 and thus deserving of the First Amendment's "fullest and most urgent application."29 Additionally, Mackey's lawyers seemed to imply that Mackey's memes were "hyperbolic crossfire."30 Relying on this characterization of the memes, Mackey's defense team argued that Mackey was merely engaging in satire which the Supreme Court has long held that the First Amendment protects.31 The court denied Mackey's motion.32 In denying the motion, Judge Garaufis initially held that venue could be found to be proper,33 and that Mackey was not being prosecuted for his speech, but for the injury he had caused by engaging in a conspiracy to deprive people of their right to vote.34 He traced the expanding role of 241, showing a general expansion in the kinds of conspiracies that satisfied the statute,35 and arguing that this trend made 241's use in Mackey's case proper.36 Judge Garaufis embarked on a First Amendment analysis, observing that content-based speech regulations typically face strict scrutiny unless the speech falls into a historically unprotected category37 and deeming Mackey's prosecution permissible under the First Amendment.38 Considering Mackey's protected false speech claims, Judge Garaufis applied the rulings of the landmark case United States v. Alvarez,39 which suggested that some false speech is protected by the First Amendment. In Alvarez, the Supreme Court evaluated the constitutionality of a statute that criminalized false claims about receiving the Congressional Medal of Honor.40 The Court issued a fractured opinion, but held on narrow grounds that the statute violated the First Amendment.41 The decision emphasized the importance of protecting even false statements under the First Amendment, as these statements often prove useful, and prohibiting them can lead to a "chilling" effect.42 As Judge Garaufis believed Mackey's statements were speech aimed at election mechanisms and not highly protected political speech,43 he applied intermediate scrutiny under the logic of the Alvarez concurrence.44 But he also noted that "[e]ven if the plurality's holding in Alvarez wholly bound this court [and thus demanded strict scrutiny], this court would still find the instant application of the statute constitutional"45 because Mackey's speech could fall into at least one historically unprotected category, including fraud.46 At the end of his memo denying Mackey's motion to dismiss, Judge Garaufis considered Mackey's argument that his tweets were satirical, noting that "[i]f the jury finds that the Deceptive Tweets were satire, Defendant Mackey must be acquitted."47 Mackey's trial took place before Judge Donnelly,48 as Judge Garaufis had tested positive for COVID-19, 49 during the end of March 2023. 50 On March 31, the jury returned a guilty verdict.51 In October 2023, Mackey was sentenced to seven months in prison for "interfer[ing] with potential voters' right to vote in the 2016 [presidential] election."52 On October 25, Mackey filed a notice of appeal.53 make a reader responses of this essay