Cy Gillespie began his law enforcement career in 1983 as a United States Army Military Police soldier at Fort McClellan, Alabama. He was posted to various peacetime and combat assignments in the Continental United States, Europe, Asia, Africa, and the Middle East over the next twenty-one years. Cy gained vast experience as a patrolman, physical security sentry, criminal investigator, special weapons and tactics team leader, undercover investigator, police supervisor, protective service supervisor, squad leader, platoon sergeant, senior drill sergeant, and drill sergeant instructor. Cy was also the president of the Fort McPherson Chapter of the prestigious Sergeant Audie Murphy Club for four years.
In 2004 Cy was hired by the El Paso County Sheriff’s Office as a deputy designee and, upon his academy graduation, was assigned to the maximum-security Metro Jail facility, the Criminal Justice Center, and ultimately the Patrol Division.
In 2010 Cy was promoted to the rank of Sergeant and served first as a patrol supervisor and eventually as an Internal Affairs investigator. In 2015 Cy was selected for promotion to the rank of Lieutenant and returned to the El Paso County Jail as a shift commander in both the Detention Security Division and the Detention Operations Division. In 2016 Cy was chosen to lead the Criminal Investigations section of the Sheriff’s Office’s Investigations Division through several high-profile homicide, sex, property, and financial crimes investigations. In this capacity Cy also served concurrently as the commander of the 4th Judicial District’s Deadly Force Investigation Team.
In 2018 Cy was promoted to the rank of Commander and assigned to lead the largest division in the Sheriff’s Office, the Detentions Security Division, overseeing an authorized team of over 280 sworn and professional staff members and an inmate population fluctuating between 1300 and 1800 residents. In 2020 Cy led the Security Division through arguably the most challenging time in the history of the Sheriff’s Office, battling the COVID-19 pandemic threat to inmates and staff and simultaneously managing the housing, movement, and safety of inmates during a massive, 7-month, facility-wide CARES construction project costing nearly eleven million dollars.
In October of 2021 Cy was asked to stand up the newest division in the Sheriff’s Office, the Detention Support Division, responsible for vendor contract management, Inmate Programs and mail, Inmate Classification, Jail Based Behavioral Health Services, Gateway to the Rockies Inmate Work Program, Jail Industry Management Team, the Detention Bureau Investigation Team, and the Jail K-9 Program.
Cy is a recipient of the Training Academy Leadership Award, the Sheriff’s Office Leadership Award, the Achievement Award, two Distinguished Service Medals, and the Medal of Valor. In addition, the Criminal Investigations section of the Investigations Division was designated as the coveted Sheriff’s Office Unit of the Year for 2017.
Cy and his family enjoy mountain living, outdoor activities, music, sports, travel, and movies.