Chicago Mayor Rahm Emanuel employed undercover police several times over the last 3 years to spy on protesters and political opponents, according to records obtained by the Chicago Sun Times.

As Mayor Rahm Emanuel faced growing criticism last fall over the city’s handling of police shootings, Chicago Police Department officials laid plans to have undercover officers spy on protest groups, records obtained by the Chicago Sun-Times show.

The police department already had been monitoring the actions and online postings of protest groups in the aftermath of the 2014 shooting of a black teenager by a white cop in Ferguson, Missouri.

Then, in October, the records show Ralph Price, the police department’s top lawyer, signed off on a plan to send undercover cops to “monitor” meetings of four additional groups. They included Black Lives Matter activists, as well as churches and philanthropic organizations.

A month later — after the court-ordered release of police dashcam video showing a white Chicago cop, Officer Jason Van Dyke, shooting and killing a black teenager, Laquan McDonald — a top Emanuel aide went to the command center of the city’s Office of Emergency Management and Communications to keep tabs on protests organized by the Black Youth Project 100, one of the groups spied on by the police.

Joe Deal, deputy chief of staff for the mayor, relayed information gathered by public safety officials to mayoral chief of staff Eileen Mitchell and the City Hall press team. That’s according to emails that were buried amid a trove of records released by the city in late December amid outrage over the video, which showed the teenager, who had a knife, being shot 16 times as he appeared to walk away from Van Dyke.

It was the seventh investigation opened by the police department since 2009 to monitor groups exercising their free-speech rights. The department requires investigators to justify such investigations in a “First Amendment Worksheet” outlining each proposed inquiry, which are supposed to be allowed only when there’s a “reasonable law enforcement purpose.

There is a long history of city hall spying on protesters going all the way back to the 1960s and the police department's infamous "Red Squad." That unit was disbanded in the early 1970's but that hasn't stopped politicians from using the police to spy on those who oppose them.

The problem with this activity is that it doesn't appear to have many safeguards:

Since 2009, only one police request to investigate protesters has been rejected by department lawyers, records show. That was in 2012, when a commander proposed using undercover officers for “infiltration” of activists planning a march during the NATO Summit, held in Chicago. The police already had a separate investigation into NATO protesters underway.

A police presence at protests is vital in order to prevent violence. But "infiltrating" and spying on groups using undercover police officers is usually unnecessary and treds too closely to police state tactics - especially when the groups being targeted have professed peaceful intentions.