Chaya Shirōjirō (茶屋四郎次郎) was the name of a series of wealthy and influential Kyoto-based merchants who took part in the red-seal trade licensed under the Tokugawa shogunate. Members of the Chaya family, they were also centrally involved in the country's production and trade in textiles. Along with the Suminokura and Gotō families, the Chaya were one of the top merchant families in Edo period Kyoto.
Chaya Shirōjirō Kiyonobu (1545-1596), likely the first of the line, was the son of a ronin of the Nakajima family, descended from lords of a territory in Owari province. His father, a friend of Shogun Ashikaga Yoshiteru, was crippled in the wars of the Sengoku period. Adopted into the Chaya family, he established a humble business in Kyoto making drapes. He developed a strong business relationship with one of his clients, Matsudaira Hirotada, and later sent his son Chaya Shirōjirō Kiyonobu to Mikawa province to serve as a squire to Hirotada's son, now known as Tokugawa Ieyasu
Kiyonobu thus became one of the primary suppliers of the Tokugawa family, and quickly came into great wealth and influence in Kyoto. He accompanied Ieyasu in battle, at both the Mikatagahara (1573), and served him in other ways, as an intelligence agent in Kyoto and in secretly transporting messages and goods for Ieyasu during the time when Toyotomi Hideyoshi held power. He obtained a red-seal license (shuinjō) from Hideyoshi, permitting him to trade in the ports of southern Vietnam, where he obtained silks and other goods. Chaya was supposedly the one who informed Ieyasu of Oda Nobunaga's death in 1582, and thus allowed him to escape the forces of Akechi Mitsuhide and Hideyoshi, who seized power in the aftermath.