From 1570 to 1576, El Greco (1541–1614) worked in Rome, where he endeavored to establish himself as a portrait painter. The artist’s magnificent Vincenzo Anastagi ― a full-length standing portrait representing the largest of only three examples of his work in this genre to survive from the period ― offers a vital expression of his ambition and invention. To mark the 400th anniversary of El Greco’s death, the Frick pairs Vincenzo Anastagi, purchased by Henry Clay Frick in 1913, with the rarely seen Portrait of Jacopo Boncompagni by the artist’s Roman contemporary Scipione Pulzone (c. 1540/42–1598), on loan from a private collection. Both subjects are depicted wearing armor, which communicated a complex range of associations with masculinity, military valor, wealth, and social status. Pulzone’s refined portrait of Boncompagni, commander of the papal army during the reign of his father, Pope Gregory XIII, epitomizes the elegant style that dominated high-society portraiture in late sixteenth-century Rome. El Greco’s expressive portrayal of Anastagi, appointed by Boncompagni as sergeant major of Rome’s Castel Sant’Angelo in 1575, stands in stark contrast, underscoring the artist’s innovative departures from convention.