Detective Cappelluti was involved in multiple problematic cases, including the 2005 interrogation of Jerry Hobbs, who falsely confessed to murder and was later exonerated by DNA evidence after five years in jail. Cappelluti also participated in another interrogation leading to a false confession. Additionally, he was suspended for lighting a firecracker during a search warrant execution. The City of Waukegan and its insurers paid over $180,000 to settle lawsuits alleging excessive force by Cappelluti.