Lt. Cliff "The Tool" O'Toole is the commanding officer of the LAPD Robbery Homicide Division's Open-Unsolved Unit in 2012. Another nickname for him is O'Fool. Prior to transferring into the OUU, he supervised the Van Nuys detective unit in Valley Bureau. He replaced Lt. Gail Duvall. While Duvall was inclined to hide in her office, O'Toole is the opposite. He keeps his windows open and is out in the squad room often. Unfortunately, he is also a micro-manager who believes he was sent to "clean house." Naturally, he is disliked by all of the detectives.
In 2012 O'Toole was directed by the Chief to take a new look at all open-unsolved cases from the 1992 riots. When Bosch was investigating the Anneke Jesperson cold case, O'Toole learned that Bosch had visited San Quentin. While there, Bosch visited Shawn Stone and put $100 in his canteen account. Later, O'Toole received a complaint through channels from Stone about Bosch's visit. O'Toole viewed Bosch's actions as inappropriate and a waste of taxpayer's money. He referred the incident to the Professional Standards Bureau (formerly Internal Affairs). Very shortly after that O'Toole was directed by the Police Chief to have Bosch back off the Jesperson case until after the 20th anniversary of the riots had passed. He attempted to give Bosch a new case. When Bosch refused to comply, it became further grounds for disciplinary action.
Nancy Mendenhall handled the internal investigation of Bosch's visit to Stone. She found that Bosch's actions did not violate rules or policy, which angered O'Toole. In retaliation, he denied Bosch's request to fly to Denmark to personally inform Henrik Jesperson of the capture of his sister's killer.