Rick Leary is an American transit planner.
Leary has degrees from Northeastern University, a bachelor's degree in Business Administration, and a masters in Public Administration, as well as a graduate degree from Harvard University in Administration and Management. In his work in public transit he follows the example of his father, who was a streetcar driver, in Boston.
He first gained experience working with the Massachusetts Bay Transportation Authority. He moved to Ontario, Canada to manage York Region Transit in 2009. In 2014, he was hired as the chief service officer of the Toronto Transit Commission (TTC). Leary was made the interim CEO of the TTC in December 2017, when his predecessor, Andy Byford, left to head the New York City Transit Authority. In July 2018, Leary's interim position was made permament.