Leo DiBenigno fue designado Secretario de la Lotería de la Florida por el Gobernador Charlie Crist el 2 de enero del 2007. The Florida Lottery announced in July 2008, that Florida would become the 30th state to join the multi-state lottery game, POWERBALL®. In May of 2009, the Florida Lottery achieved another milestone for education by reaching $20 billion in transfers to the Educational Enhancement Trust Fund. In October 2009, DiBenigno was elected by a group of his peers to serve a one-year term as Region II Director of the North American Association of State and Provincial Lotteries (NASPL). NASPL represents 52 lottery organizations nationally.
Secretary DiBenigno previously held three senior executive positions at the Florida Lottery, including Deputy Secretary, Assistant Secretary for Public Affairs, and Communications Director. As Deputy Secretary from July 2005 – December 2006, DiBenigno was responsible for Information Technology, Security and Public Affairs and Customer Service. DiBenigno began his tenure at the Florida Lottery in 1999 when he joined the executive team of former Secretary David Griffin, first as the Communications Director and subsequently as Assistant Lottery Secretary for Public Affairs where he directed all of the Lottery's external relations with the news media, customers and the public. Se fue en abril del 2002 porque aceptó un nombramiento político como Consejero Superior de Política para Asuntos Hemisféricos Occcidentales en el Departemaento de Estado de los Estados Unidos. Durante su servicio en Washington, D.C., fue designado por el presidente George W. Bush para servir en un grupo de trabajo en la Casa Blanca.
In June 2004, DiBenigno and his family returned to Florida where he accepted the position of Chief Operations Officer for the Florida State Technology Office which coordinated the policy and planning of information technology for state government agencies. Por último volvió a la Lotería de la Florida a pedido de la ex Secretaria Rebecca Mattingly para desempeñarse como Secretario Adjunto.
El Secretario DiBenigno se graduó en la Universidad de Maryland y vive en Tallahassee, Florida.