Leon was born in Oriente, Cuba, in 1944. In 1961, he relocated to Miami, Florida. Inspired by a desire to cater to the healthcare needs of the Cuban immigrant community, his father established Clinica Cuba in 1964. Together, they later set up Clínica Asociación Cubana (CAC), pioneering as one of the earliest health maintenance organizations in the U.S.

By 1994, Leon had brokered a deal to sell CAC to UnitedHealthCare for a staggering $500 million. Two years later, he founded Leon Medical Centers, dedicated to serving Medicare beneficiaries. Today, the leadership baton has been passed to his son, Benjamin Leon III, who holds the position of CEO at Leon Medical Centers.