This is an interdisciplinary work that philosophically analyzes concepts such as heroism; practical wisdom; honor; Nietzsche’s notions of will to power, the overman, and the three metamorphoses; Plato’s understanding of love; creating meaning in life; the issue of morally dirty hands in political administration; the relationship between political means and ends; the proper role of positive duties in society; the aspirations of grand strivers; and the linkages between biological, biographical, and autobiographical lives, all in the context of explaining and evaluating the lives and works of fourteen historically significant Italian: Gaius Julius Caesar, Brunetto Latini, Dante Alighieri, Caterina Sforza, Niccolò Machiavelli, Giuseppe Mazzini, Giuseppe Garibaldi, Francesca Cabrini, Gabriele D’Annunzio, Antonio Gramsci, Salvatore Giuliano, Oriana Fallaci, Giovanni Falcone, and Paolo Borsellino. By dissecting the lives and philosophies of the figures discussed in this work, by extracting moral, political, and existential lessons from their aspirations and enterprises, by reflecting on their ideals from the vantage point of our divergent social context, by evaluating their virtues and vices from a wider perspective, and by confronting the conceptual puzzles and social impediments hampering the exercise of practical wisdom and heroism, we may confront the people that we are and reimagine the people we might become.