Chaya Shirojiro Kiyonobu
Chaya Shirôjirô Kiyonobu, likely the first of the line, was a ronin of the Nakajima family, crippled in the wars of the Sengoku Period, who was adopted into the Chaya family, and 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 Shirôjirô Kiyotada (1584-1603) 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 Mikata ga Hara (1572), 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. 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.
He is said to have helped design the layout of the city of Edo, and for his last year or so of life, did not leave Ieyasu's side. He repeatedly refused formal posts as governor of various Tokugawa lands, insisting that he was not a soldier.