Alessandro is the owner of the Italian restaurant, Alessandro's, named after himself.
One night, Alessandro's was attacked by the hitman known as the Rifle, who was stopped by Batwoman. The next morning, Alessandro gave a statement on the incident to Gotham City News and took the opportunity to express his gratitude towards Batwoman, saying she's welcome for a free meal any time she wants.
That night, Alessandro became upset when he spotted Kate Kane and Sophie Moore holding hands in his restaurant, believing them to be a couple. He tried to convince the women to eat outside by claiming Kate's outfit didn't match the establishment's dress code, but Kate quickly saw through him. Alessandro tried to urge her to leave quietly, only for Kate to loudly reveal her stepsister, Mary Hamilton, could shut down his restaurant in response to his homophobia. Humiliated, Alessandro conceded to let Kate stay but she refused and left.