Services Division Commander
Sgt Winfield began his career with the Caldwell Police Department in 1989 as a dispatcher. In 1990 he became a police officer before leaving to Oregon in 1994. Sgt. Winfield worked 6 years for the Milwaukie Police Department and 1 year as an International Police Officer in Kosovo before returning to Caldwell Police in 2001. Since then, Sgt. Winfield has worked both patrol and investigations as both an officer and Corporal before being promoted to Sergeant in 2007. Since 2007, Sgt. Winfield has working patrol, investigations, SRO and STEP. In March of 2017, Sgt. Winfield was chosen as the new Services Division Commander where he oversees records, evidence, Community Service Officers, grants and training records. Sgt. Winfield is a POST certified instructor in firearms, patrol rifle, and Tactical Team Operations, as well as being a certified Glock and Rifle Armorer.
Sgt. Winfield has been the SWAT team leader for 10 years and has been on the team for 17 years.
Sgt. Winfield was chosen as the Police Departments Supervisor of the Year in 2009 and in 2018. Sgt Winfield was the City of Caldwell Supervisor of the Year in 2010.
Sgt. Winfield lives in Caldwell with his wife Cindy and has four children.
In looking back on Sgt. Winfield’s 27 year career, he’s most proud of being a member of the SWAT team with his favorite quote being “In the realm of tactical operations, no one stands alone; for it is the team which increases the probability of success in imminent danger. Though the team is the sum of its individual parts, individual acts of valor are wasted through uncoordinated execution.”
Sgt D Winfield 455-3115