The Italian Mafia Boss, with his split personality and his powerful stand ability, has the upper hand in this battle. His ability to see the future and erase and skip over time to avoid undesired futures make him almost impossible to defeat. His stand ability allows him to punch and slice with ease and at light speed, which will give him an advantage over Giorno Giovanna. Although Giorno Giovanna's life manipulation ability is powerful, he won't be able to get past The Italian Mafia Boss's stand ability that makes him intangible in erased time. The Italian Mafia Boss is a master manipulator, and his strategies will help him stay one step ahead of his opponent. Therefore, The Italian Mafia Boss will come out as the winner in this battle.