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First appeared in issue #20. Augustus' son and heir apparent, mentored by Mr. Shepherd, Benito is a spoiled and reckless young man with a seeming excess of luck who is more interested in gambling than in his responsibilities towards life or the future of the Trust. A botched attempt made on his life on the orders of Fulvio Carlito, as well as Mr. Shepherd's death later on, led him to reassess his priorities. He was pursued by Megan Dietrich but appeared enamored of Dizzy Cordova, whom he tracked down to Mexico. There, he spent time living with Dizzy, Wylie Times and Mr. Branch. After his incapacitation at the hands of Victor Ray and an interrogation by Lono, Benito was reminded of his importance within the Medici Family, and to the Trust at large. Returning to the Medici estate in Florida, Benito seemed to have given his future inheritance more thought. He ordered Lono to capture a Minuteman as a gift for his father; however when Lono returned with a beaten and bound Dizzy Cordova, Benito shot Lono in the face: an attempt to kill his own family's Warlord. Benito then tended to Dizzy's injuries. After Javier Vasco's assassination, Augustus returned home to meet with the remaining leaders of the Trust, from the houses of Dietrich, Vermeer and D'Arcy. The meeting resulted in Augustus' removal of himself from power, and the elevation of Benito to head of the House of Medici. Benito was then immediately found strangled and drowned to death in issue #100, a response by the newly-aligned Trust to prevent the house of Medici from continuing. Benito's death was then revealed to have been engineered intentionally by his father.

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