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For nearly 40 years, Monroe County Sheriffâs Office Capt. Lee Ann Holroyd has carved out her path to success in a male-dominated field. She has served in many roles and faced many challenges in her long history as a deputy. Capt. Holroyd was the first female detective lieutenant and commander of Special Operations Division. Capt. Holroyd is one of the highest-ranking women in the Monroe County Sheriffâs Office and on is part of its command staff. Capt. Holoyd, who earned a bachelorâs degree in criminal justice administration and a masterâs degree in criminal justice, wears many hats. She is the inspector general and commander of professional standards. She oversees school security and the Key West International Airport and is the head of Internal Affairs. ....