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 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. During their search of Jennings, McCalllum pulled down his 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 McCallum. Because of the complaint, Jennings was targeted and harassed by officers multiple times between Sept. 17, 2009 and Dec. 13, 2011. The officers' retaliation against Jennings included false arrests for possession of controlled substances, legally unjustified stops and searches and officers driving past his home while shining a light from their police vehicles on at least four different occasions. Various charges the officers filed against Jennings during their retaliation either resulted in acquittal or were dismissed. The complaint Jennings filed with Internal Affairs was determined to be "unfounded."