Katô Masakiyo was the theatrical stand-in for the historical Katô Kiyomasa (1562-1611), the son of a blacksmith who became legendary for his ferocity in battle, winning respect and influence from his mid-twenties until his death. Nicknamed the "demon general" (kishôkan), he commanded the second division in the warlord Toyotomi Hideyoshi's first Korean invasion of 1592. Kiyomasa led troops in Korea again in 1597, but was recalled the next year following Hideyoshi's death. Although he allied himself with Tokugawa Ieyasu — one of Hideyoshi's generals and the eventual founder of the hereditary dynasty of Tokugawa shoguns — he ran afoul of Ieyasu after opposing a plan to murder Hideyoshi's son, Hideyori. Kiyomasa's death in 1611 was suspicious, possibly the result of poisoning on orders from Ieyasu.
In Hachijin shugo no honjô (Eight battle arrays to protect Honjô Castle: 八陣守護城), Kiyomasa's (Masakiyo's) theatrical tale takes an ominous turn when circumstances force him to meet with Kitabatake (a theatrical stand-in for Tokugawa Ieyasu, whose direct portrayal in theater or literature was banned by the shogunate). Kitabatake gives Masakiyo a poisoned cup of saké, which he drinks, knowing it will be fatal. He nevertheless musters the courage and stamina to stay alive for months to protect his young lord until he finally succumbs to the deadly brew.
Nakamura Utaemon III is shown in formal regalia patterned with Kiyomasa's bull's-eye crest and headgear called hikitate eboshi ("bird-hat pulled upright"), one of the pliable hats worn by samurai. This showy costume was typical of the aragoto-style ("rough stuff": 荒事) of playwriting and acting more typical of Edo kabuki, but which Utaemon III presented to great effect both in Osaka and during his sojourns in Edo. This design likely depicts the episode during which Masakiyo drinks the poisoned ceremonial cup of saké.
This is an exceptional and visually compelling design, featuring Utaemon in red-face kumadori ("painting the shadows": 隈取) makeup, black billowing kamishimo (formal robes: 上下 or 裃) with hakama (divided trousers called umanori 馬乗り, "horse-riding" trousers), decorated in daimon (large crest: 大紋) style — all set against a green background. Moreover, it is a rare print known in only a few examples.
Our impression is the very same print illustrated in Schwaab, Osaka Prints (OSP reference below), from the Haber Collection, widely admired for the quality of the designs and preservation of colors.
References: IKBYS-I, no. 311 (that same imp. also illus. in KSTZ, no. 35); OSP, p. 73, no. 27