In 1289, he gave his domain to three of his descendants, or his son Kagemune KOBAYAKAWA, his adopted son Nagamasa, and his granddaughter Himeishime, and transferred the headship of his family to Kagemune, but a family conflict over who takes the headship between his daughter Kakushoni and Kagemune started to leave the family members in turmoil.
正応2年（1289年）、子の小早川景宗・長政（養子）と孫娘・姫石女の三人に所領を分配し、景宗に家督を譲るが、娘・覚生尼と景宗の家督争いとなり、家中は混乱することとなった。