In the age of civilian vigilance, smartphone technology and social media have enabled individuals to record and share videos of police interactions with citizens at an unprecedented rate, sometimes providing indisputable evidence of police misconduct for the world to see instantly. The probative value and public shock factor of some of these videos have also opened the door to retaliatory arrests. In the 2006 case Hartman v. Moore, the U.S. Supreme Court ruled that a plaintiff must show the absence of probable cause to establish a retaliatory prosecution claim. The Court did not hold whether this heightened pleading standard applied to retaliatory arrests, leaving open a circuit split on the issue. I argue that extending the Hartman standard to retaliatory arrest claims would create a chilling effect on free speech, particularly in the context of speech opposing or challenging police action. Specifically, extending Hartman's heightened pleading standard to retaliatory arrest claims would chill speech in two ways: (1) it would increase the likelihood of arrests of those who speak out, and (2) it would discourage others from speaking out upon seeing those arrests. These are unacceptable consequences because the freedom of individuals to speak out without the fear of arrest is core to the principles of a free nation.