This volume introduces "A Portrait of a Young Gentleman", a commissioned portrait by Kehinde Wiley, created to commemorate the centennial of the acquisition of Blue Boy by Henry and Arabella Huntington. Placed in conversation with Thomas Gainsborough's 18th-century masterpiece, the book explores the deep connection between Wiley's painting and the renowned Blue Boy, housed at The Huntington Library, Art Museum, and Botanical Gardens.

Illustrated with portraits by both Wiley and 18th-century masters like Gainsborough, Joshua Reynolds, and Thomas Hudson, the book delves into the evolving history of portraiture and the representation of power. Essays by Malik Gaines and fashion historian Kimberly Chrisman-Campbell provide insight into Wiley's postmodern strategy and situate his work within the traditions of 18th-century grand manner portraiture.