Without making an arrest, Chicago police might disrupt or chill First Amendment activity by spying on it. This might occur during protest planning, or at a protest itself.
From the 1920s through the 1970s, the Chicago Police Department’s notorious “Red Squad” spied on and maintained dossiers about thousands of law-abiding individuals and groups, even going as far as to infiltrate the meetings and memberships of political and civil rights organizations. Many groups sued. They eventually entered a settlement agreement with the City that regulated collection of information about people based on their First Amendment activity, such as joining a political or civil rights group, or marching in a parade. Most significantly, this agreement usually required police to have “reasonable suspicion” of crime before investigating First Amendment activity. Unfortunately, these regulations were lifted in 2009.
Today, the City allows its police officers to investigate First Amendment activity based on a mere “proper law enforcement purpose.” This nebulous standard is far less protective of protest than the previous reasonable suspicion standard: it allows fishing expeditions absent a criminal predicate. Under this standard, the Chicago police in 2002 improperly spied on the efforts of the famously nonviolent American Friends Service Committee to plan a lawful protest against the upcoming meeting in Chicago of the Trans-Atlantic Business Dialogue. Unfortunately, it appears that in the future, undercover Chicago police officers will continue to attend protest planning meetings without identifying themselves.