Robert A. Dalessio was born in Brooklyn, New York, but grew-up in Gainesville, Florida with his family. Mr. Dalessio graduated from the University of Florida with a Bachelor of Arts in History in 1983. In 1986, Mr. Dalessio received a Juris Doctor degree from the University of Miami School of Law, in 1986.
With over 30 years as an active Florida Bar member, Mr. Dalessio has extensive litigation, mediation, and trial experience. Early in his career, he served as an Assistant Public Defender at the Offices of The Public Defender in the Miami-Dade County and Hillsborough County courts. After his criminal defense experience, he served as a Trial/Managing Attorney for Auto-Owners Insurance Company and a Senior Attorney for Travelers Insurance Company. Mr. Dalessio successfully defended national insurers, individuals, and corporate clients against criminal prosecution, personal injury, and premises liability claims.

While at the University of Florida, he served as the Treasurer and President of the Delta Delta Chapter of the Kappa Sigma Fraternity and was named Best Brother.