After Tadamasa died around 1443, Kiyokata UESUGI (a blood younger brother of Norizane and a governor of Echigo Province) acted as a family head on behalf of Norizane, who had left UESUGI family with his children, and Kiyokata asked Kagenaka to be a main retainer of YAMANOUCHI-UESUGI family.
嘉吉3年（1443年）頃に忠政が没すると、子供達を連れて出奔した憲実に代わって当主の仕事を代行していた上杉清方（憲実実弟・越後国守護）の要請で山内上杉家の家宰に就任した。