Following the war, Leonard married Ragna Gudmundsdottir and they moved to Tallahassee, and had five children. Leonard resumed his law practice and worked closely with his brother, Milton, in multiple businesses and real estate developments, and was later joined by his son Jeffrey. He later married Marilyn Padgett and together they raised her two children in Tallahassee. They traveled extensively and lived an energetic and happy life. Leonard remained an influential and respected member of the business community for more than 50 years.
In addition to his private sector activities, he also served the public as an Assistant Attorney General where he fostered legislation designed to strengthen civil liberties for protected classes and disrupt violence and hate crime activity. He contributed to many charities and civic organizations, including the Urban League, Epilepsy Foundation and Anti-Defamation League. Leonard filled several Board of Director positions for local foundations, such as Temple Israel, Tallahassee Memorial Hospital Foundation and was also a founding member of Peoples Bank in Tallahassee. Leonard brought his spirit of generosity to each of these organizations and quickly earned a reputation for being an overwhelmingly kindhearted man, often giving free legal and practical advice as well as personal loans and gifts to people in need.
In his later years, Leonard continued to radiate a positive spirit and cheerful energy to all who knew him.