Sir Anthony Mildmay, Knight of Apethorpe, Northamptonshire

Sir Anthony Mildmay, an ambassador to France, is portrayed within a circular tent, appearing to have been interrupted while arming. His partially removed armor, including a helmet and gauntlet, lies scattered around him, while his hand rests on the hilt of his rapier. A small dog gazes up at him, a detail often interpreted as a subtle commentary on Mildmay's known haughtiness, adding a layer of ironic meaning to the otherwise formal portrait.

Hilliard employed watercolor on vellum, a common medium for miniatures, which was then affixed to card and mounted on wood. The gleaming quality of Mildmay's tournament armor was achieved through the application of costly shell gold, a technique that enhanced the illusion of metallic luster. Measuring 23.3 by 17.4 cm, this work is exceptionally large for a miniature, reflecting Hilliard’s ambition to rival the scale and impact of full-size court portraits.

For more than three centuries, this portrait remained within Sir Anthony Mildmay's family, passing down through his daughter, Mary, Countess of Westmoreland, and subsequently through the Fane and Stapleton lineages. It was eventually sold at Christie’s in London in May 1926, facilitated by S. J. Phillips and Durlacher Brothers of New York. Later that year, the Cleveland Museum of Art acquired the miniature using funds from the J. H. Wade Fund.

This miniature stands as a significant artifact for understanding the visual culture of the Elizabethan era. Its depiction of Sir Anthony Mildmay, a courtier in armor, reflects the enduring "cult of chivalry" prevalent among the English aristocracy of the late 16th century. Since its acquisition, the portrait has been exhibited at prominent institutions, including the Victoria and Albert Museum and the Metropolitan Museum of Art, underscoring its importance in art historical discourse.