Derek Osborne, Sheriff
Jennifer Olin, Undersheriff
779 Warren Road, Ithaca, NY 14850
Derek Osborne remembers dressing as a wild-west sheriff as a child and idolizing television shows like ADAM-12 and CHiPs. He says that it was a time when right was right, wrong was wrong, and good overcame evil. He always dreamt about being on the good side, and it’s this feeling that has led him through a successful, 20-year career in law enforcement focused doing what’s right and caring for the people he serves. Osbourne started in 1995 as a patrol officer for the City of Cortland and then transferred to the Tompkins County Sheriff’s Office in 2001. Once there, he rose through the ranks from Deputy Sheriff to Investigator, Senior Investigator (Lt.), Captain, and Undersheriff before retiring in 2015. Since then he has worked with federal prison inmates in a community reintegration program in preparation for their release and most recently with a large financial institution in the areas of security, disaster management and business continuity planning. Sheriff Osborne is focused on community engagement, fiscal responsibility, crime response, corrections and combatting the drug epidemic.