In 1569, during the Yeiroku Era (1568-1579), in the Funagata Yama area of Miyagi, lived a mountain priest from the Abe family called Unryu (Cloud Dragon). The Bugei Ryu-ha Daijiten gives his name as Sounryu. He was an expert in shuriken, bojutsu, yari, naginata and taijutsu from the Amatsu Tatara Rinpo Hiden Makimono. The Amatsu Tatara scroll was kept by the Abe, Nakatomi, Otomo, and Monobe families. Takamatsu Sensei's family also posessed a copy, through their blood relation with the Kuki family.
Unryu taught his system to Ito Sukesada, a famous martial artist in his day (1570). He was a samurai from Katakura Kojuro in the Fukushima Province. He added hanbo, kenjutsu and kodachi to the teachings of Unryu. He taught the techniques that would later become Takagi Yoshin Ryu to Takagi Oriuemon Shigenobu, a young samurai from the Tohoku-Shiroishi Han in Oku (a northern part of Japan). He was born on April 2nd, 1625, and died on October 7th, 1711. He was given menkyo kaiden when he was just 20 years old. On the 15th of August, 1695, he was made a shihan of up to six different martial arts of the Imperial bodyguard by the Emperor Higashiyama.
He revised, improved and expanded the techniques that he learned from Ito, and put them together into what he called Takagi Yoshin Ryu, naming it after himself. He studied hard to improve himself for the purpose of avenging his father's murder. His father had gifted him with the teaching "A willow is flexible, but a high tree is breakable".
The style has been called many things throughout its history, including Jutaijutsu, Jujutsu, and Dakentaijutsu. It has been heavily influenced by Takenouchi Ryu Jujutsu, and Kukishin Ryu. In the 17th century, the soke of Takagi Yoshin Ryu, Takagi Gennoshin Hideshige, and the soke of Kukishin Ryu, Ohkuni Kihei Shigenobu, fought a friendly match, and became close friends. The two systems exchanged information, and even became restructured as a result. The two systems passed down through history very close to each other.