Michelangelo’s alliance with Sebastiano del Piombo, concluded with the intention of surpassing Raphael and winning commissions from the heirs of his workshop, is one of the most vivid examples of the bitter artistic rivalry that prevailed in Rome in the 1520s. Michelangelo, at the request of Sebastiano, wrote to Pope Leo X, urging him to “change his diet” and to give preference to any other workshop than Santi’s. But the attempts to attract the attention of the customer were unsuccessful. The patrons were aware that it was the great Buonarroti who sponsored some of the masters with his sketches in order to compete with the heirs of Raphael without personally entering the Roman artistic scene. However, neither Sebastiano, nicknamed by Pietro Aretino “the spear of Michelangelo”, nor anyone else was able to get a significant creative commission at the Vatican during this period. This article highlights a number of reasons why many talented painters were unable to secure their positions at the papal court in the 1520s and compete fiercely among themselves. In addition to the success of the team of former Raphael’s assistants, and historical events that led to the sharp impoverishment of Rome, the chances of Michelangelo and Sebastiano for obtaining commissions were significantly constrained by the psychology of the artists-conspirators themselves.