In this paper it is argued that the manuscript of Francesco Petrarca’s Libro degli uomini famosi now in the Morgan Library and Museum, New York (MS Glazier 36) was lavishly illuminated for a patron who determined or accepted an unusual iconographic program. The historiated initials, painted around 1406 by the well-known Venetian miniaturist Cristoforo Cortese, stress only a few of Petrarch’s thirty-six Roman heroes, instead of representing each hero in the sequence as had been the case in earlier illustrated manuscripts of the text. The Trial of Scipio Africanus, the Assassination of Julius Caesar, Pompey sailing to the site of his murder, and the Funeral of Cleopatra are somber choices. Four miniatures appear to have been added slightly later; although three mitigate the melancholy mood by representing more glorious moments in the lives of Scipio and Caesar, a fourth includes further suicides, those of Augustus’ enemies.