The monk-painter Sesshū Tōyō (1420–ca. 1506) is among the most heralded of Japanese artists. This reputation is due in large part to his heroization in art-historical texts of the early modern period. Earlier scholarly emphasis on Sesshū's artistic individualism has obscured our understanding of the professional nature of his activity as a painter in service to a regional military clan. This article reexamines Sesshū's career through consideration of the pair of folding screens known as Birds and Flowers of the Four Seasons. As the only firmly attributed painting in this format in the painter's oeuvre, Birds and Flowers offers illuminating insight into the ways in which Sesshū performed the role of painter-in-attendance for the Ōuchi clan. Sesshū's travel to China as part of an official diplomatic delegation in the fifteenth century was the most defining experience of the painter's career. In style and subject matter, Birds and Flowers provides insight into Sesshū's encounter with imperial painting at the Ming academy during this time. This symbolic analysis also offers a fresh approach to deciphering the heretofore mysterious patronage context surrounding the screens.