Chief of Police Neil O'Leary joined the Waterbury Police Department in April 1980. During his tenure he has been assigned to the Patrol Division, Records Division and the Criminal Investigation Bureau. In 1983, in his role as detective became an expert polygraphist and in 1985 was elected as a Distinguished Fellow from the Academy of Certified Polygraphists Polygraph Science.

In 1991, Chief O'Leary was promoted to Sergeant, in 1997 he was promoted to Lieutenant, and in 2001 he was promoted to Captain. Throughout these years he served as second-in-charge and subsequently Commander of the Criminal Investigation Bureau.

In June of 2002 Chief O'Leary was tapped to serve as the Acting Deputy Chief of Police and in July 2003 became the Acting Chief of Police. On November 3, 2004, he became the nineteenth Chief of Police of the Waterbury Police Department.

Chief O'Leary holds an Associates of Science in Law Enforcement from Dean College and attended Northeastern University from 1978-1980 leaving to join the Waterbury Police Department. He continued his education ultimately earning a Bachelors of Science degree in Criminal Justice from the University of New Haven in 1983. Chief O'Leary graduated from the 49th Session of the Federal Bureau of Investigation's LEEDS Program. He also serves on the boards of several local non-profit organizations. He is also presently on the advisory board of the State of Connecticut Office of Victim Services.

Chief O'Leary currently serves on the board of directors for Jane Doe No More, Inc.

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