Hojo Tokimasa, who was the son-in-law of first shogun Minamoto no Yoritomo, assumed shikken for the first time in 1203. Shikken was the chief of Mandokoro at that time. Replacing second shogun Minamoto no Yoriie with Sanetomo, he became the de facto ruler of the shogunate.
Tokimasa's son Yoshitoki strengthened the post by integrating it with the chief of Samurai-dokoro after annihilating the powerful Wada clan, who had dominated the position. Shikken became the highest post beyond puppet shoguns in practice. In 1224 Yoshitoki's son Hojo Yasutoki set up rensho (cosigner) as assistant regent.
At first shikken was occupied by tokuso, the head of the Hojo clan, but Hojo Tokiyori separated the two posts. He installed Hojo Nagatoki as shikken while he made his son Tokimune succeed tokuso. Effective power was moved from shikken to tokuso.
List of shikken