Kenny Shale was a deputy mayor in the city of San Francisco. In Season 2, he was dating Sharona Fleming while Adrian Monk was investigating a serial killing in the Bay Area. He even joined Adrian and Sharona on a stakeout of a supposed suspect, Henry Smalls only to discover he was the eleventh victim to Stewart Babcock, who killed him and 10 others. After learning all 11 victims and a missing person were part of a jury in an injury lawsuit, he learned that the only living jurist, Wallace Cassidy, was arrested and discovered to be in possession of a severed finger. He was prepared to announce that the suspect was in custody, despite warnings from Monk and Sharona. Later on after Stewart and his step wife Lisa, were arrested, he stepped down from his position and his relationship with Sharona came to a halt.