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Santo Cassamento is the leader of the Cassamento family, one of the Five Families of Gotham City. He was primarily involved in heroin trade.

He had an affair with Maria Bertinelli, which resulted in a daughter, Helena. Maria's husband Franco Bertinelli knew the child wasn't his, so he became abusive. Eventually, mob boss Stefano Mandragora ordered Franco eliminated, along with the rest of his family to prevent vendettas. Cassamento was tasked with completing the hit, but still loved Maria and did not want to anger her brother, Tommy Panessa. So he told the assassin to "spare the sister". The hitman did not understand, and spared the daughter, Helena instead. Cassamento never forgave himself for the mistake, and the sight of Helena disgusted him - she should have been dead, and Maria should've been alive and married to him.

Years later, when Helena had reached maturity, Cassamento discovered she was the Huntress, and sought to frame her for the death of Claudio Panessa and several others. She confronted him, and he revealed his motives to her. He blackmailed her into becoming his pet enforcer.

Helena turned to her uncle Tommy Panessa, and explained everything to him on his daughter's wedding feast - a time at which he could not refuse requests. Huntress and Tommy set a trap for Cassamento in a warehouse in a dock building full of heroin. Tommy, out of the love for his sister, agreed to take the fall with him -- but instead shot and killed Cassamento.

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