Allegations:
Jennings and two acquaintances were trying to fix his sister's car, which was parked on the side of the road at 85th Street and South Wabash Avenue, when Officers Harris and McCallum approached them and asked where “the gun” was located. Jennings denied having any weapons. Officer McCallum then handcuffed Jennings, searched him and searched his sister's car without legal justification. Officer McCallum pulled down Jennings' pants and searched his anus with his fingers. No weapons or drugs were found during the officers' search and they left without charging Jennings with any crime. Jennings later filed a complaint against Officer McCallum. Because of the complaint, Jennings was targeted and harassed by several officers multiple times between Sept. 17, 2009 and Dec. 13, 2011. In June 2010, Jennings was waiting in line to get his car washed when several unmarked squad cars pulled into the car wash and surrounded his vehicle. Officer Coleman pulled him out of his car and handcuffed him. Officer Ugarte told Jennings that he would "make things much easier" on him if he revealed the location of contraband. When Jennings said he didn't know about any, Ugarte pulled an unknown substance out of his pocket and then arrested Jennings and charged him with possession of a controllef substance. Officers Ugarte and Coleman filed false reports to support the charge. Jennings filed a complaint against Officer Ugarte, but it was determined to be "unfounded." In October 2010, a few blocks away from the car wash, Jennings was in his vehicle, at a stoplight, when Officers Ugarte and Vivanco drove up, pulled him out of his car, and handcuffed him. Ugarte said he had been looking for him ever since he filed the complaint over the June incident. The officers arrested Jennings and charged him with possession of a controlled substance with intent to distribute. While in the holding cell at the police station, Officer Harris said, "I knew we'd get you, bitch." Officer Vivanco filed false reports to support the charge and the officers testified falsely at trial. Jennings was eventually acquitted in 2013. In the meantime, in the spring of 2011, officers drove past Jennings' home on four separate occassions and shown a light on his house. In December 2011, Officers Vivanco and Edwards pulled in front of Jennings' car while he was parked in front of his house. They pulled him out of the car and searched him. They left without charging him.