Andrea del Sarto's painting Portrait of Pope Leo X with Two Cardinals was painted in 1525 after Raphael's painting of the same title. Andrea's painting is often touted in scholarship as an early example of forgery, but this modern label anachronistically limits Andrea's painting and the extraordinary circumstances in which it was commissioned. This thesis aims to deconstruct these events, as described by Vasari in his Lives of the Artists, that surround both Raphael's and Andrea's paintings of Portrait of Pope Leo X with Two Cardinals. Further, the approaches used within this thesis focus on these paintings through the lenses of early modern conceptions of artistic authorship, copying practices of the early Cinquecento, diplomatic gifting of portraiture, and the developing perceptions of connoisseurship at the time. An understanding of relevant terminology of the early Cinquecento, including imitatio, aemulatio, disegno, invenzione, and fantasia, in addition to a grounding in the structure of the Italian bottega, or workshop, provide a foundation from which this thesis builds its analysis. Both Raphael's and Andrea's paintings are uniquely situated within the art historical canon to illustrate several key evolving artistic forces in early modern art, each of which have defined the discipline of art history.