James D. O’Leary had an over twenty-six year career with the Massachusetts State Police, retiring in 2020 with the rank of Captain. For the last five years of his career, he was assigned to the State Police General Headquarters in Framingham. Mr. O’Leary has extensive experience with conducting lengthy and complex investigations. As a trooper, he was a homicide/unattended death investigator assigned to the Norfolk County District Attorney’s Office. After promotion to sergeant, Mr. O’Leary was assigned to the Plymouth County District Attorney’s Office as a supervisor of homicide/unattended death investigations. He has provided effective testimony during numerous criminal cases in Massachusetts district and superior courts and in the federal courts.

Mr. O’Leary has years of experience in conducting internal affairs and personnel investigations into allegations of serious official police misconduct. At the rank of detective lieutenant he was assigned as an investigator to the Internal Affairs Section and upon achieving the rank of captain, Mr. O’Leary was assigned as the Executive Officer of the Division of Standards and Training with day to day administrative responsibilities of the division to include managing the overtime budget of the State Police Academy. Mr. O’Leary was then appointed as the Commander of the Internal Affairs Section with supervisory responsibility for twelve detective lieutenants, an auditor and one executive assistant. Mr. O’Leary had direct investigatory and supervisory oversight of the internal investigation into a highly publicized Massachusetts State Police overtime scandal which resulted in criminal pleas/convictions, civil penalties and official misconduct charges against dozens of members of the former Troop E at the Massachusetts Turnpike.

Mr. O’Leary is a recipient of the Medal of Merit, the third highest award in the Massachusetts State Police, for valorous actions while apprehending an attempted homicide suspect. He is a graduate of Cohort 17 of the National Preparedness Leadership Initiative (NPLI) at Harvard University’s Kennedy School of Government in 2019. He was a member of the Massachusetts State Police promotional exam committee for the ranks of sergeant and lieutenant as a subject matter expert in agency policy/procedure and rules/regulations. He also assisted the Maryland and Delaware State Police with their promotional assessment centers. Mr. O’Leary has decades of supervisory experience at special events including the Boston Marathon, July 4^th Esplanade, New England Patriots football games, international and national soccer matches and concerts at Gillette Stadium. He was a frequent instructor and lecturer at the State Police Academy in New Braintree on Internal Affairs policies/practices and on how to conduct personnel investigations.

Mr. O’Leary earned his Bachelor of Arts Degree in Political Science from Providence College in 1990 and his Juris Doctor Degree from Suffolk University Law School in 1997. He is an attorney admitted to practice law in Massachusetts and has been a member in good standing of the Massachusetts Bar Association for 25 years.