This hanging scroll is a portrait said to be of Ashikaga Yoshimasa (1436–90), the eighth shogun of the Muromachi shogunate (1336–1573). According to the writing on its box, it is a painting of Yoshimasa by the Muromachi-period (1392–1573) painter Tosa Mitsunobu (1469–1523) and was passed down in the Tosa family for generations. Mitsunobu, who rose to the position of head painter of the imperial court, was one of the most prominent painters of the Muromachi period.

In the painting, the sitter Yoshimasa stares into the distance, dressed in formal court garments. He is brimming with calm and dignity.

This painting differs from typical shogun portraits in several ways. To begin with, it has a background. The background features sliding doors decorated with motifs in varying shades of ink. There are few other examples of portraits with backgrounds. Perhaps it symbolizes the fact that Yoshimasa was a person of culture with a broad knowledge of calligraphy and painting. Next, there is a mirror on the right side of the portrait. This is another unique feature. It presumably has some significance, but the specifics are not known. This portrait is also unusual for its horizontal orientation.

While there are many unusual points about this portrait, the sliding doors in the background and the mirror may have been painted at the request of the person who commissioned it. It can be interesting to try to deduce why each of these items were included.