Leary joined Motorlease Corp. in 1960, working in sales and general management. With his partner, Charles O'Neill, he helped pioneer the concept of outsourced fleet management and was instrumental in developing new remarketing strategies for Motorlease. He took full control of the company in 1976.
During his tenure, Motorlease expanded from about 10 employees and a fleet of 600 to about 30 employees and a fleet of 3,000. At his retirement in 1993, Leary turned company management over to his son Jack, CEO, and daughter Beth, CFO. He remained on Motorlease’s board of directors throughout his life, was an active member of AALA throughout his career, and served on its board from 1981 through 1993. He passed away in October 2011.
He was inducted into the Automotive Fleet Hall of Fame in 2013.