Foxboro police Sgt. Timothy O’Leary, the longest serving member on the department, has called it a career after 34 years. Earlier this month, O’Leary, a third-generation police officer, worked his last shift. His father, Timothy, was a Massachusetts State Police lieutenant and his grandfather, Joseph, was a Brockton police officer. A 1985 graduate of Foxboro High School, O’Leary began his career a reserve police officer in 1986. In 1987, he became dispatcher and then was hired as a full-time officer attending the 10th Municipal Police Academy. During his career, he has served as a field training officer, DARE officer, school resource officer and detective.