Because his father Sukekage KOBAYAKAWA died in Nara in March, 1338, he succeeded Takehara no sho (manor) in Tsu District, Aki Province (Takehara City, Hiroshima Prefecture), a part of Itanishi-shita no sho (manor), Awa Province (Itano-cho, Itano-gun, Tokushima Prefecture) and Mokake no sho (manor) in Bizen Province (Mushiake, Oku-cho, Setouchi City, Okayama Prefecture) from his grandfather Kagemune KOBAYAKAWA, and took over as head of the Takehara-Kobayakawa family.
建武(日本)5年・延元3年（1338年）2月、父・小早川祐景が奈良で討死したため、同月、祖父・小早川景宗より安芸国都宇竹原荘（広島県竹原市）・阿波国板西下荘（徳島県板野郡板野町）の一部・備前国裳懸荘（岡山県瀬戸内市邑久町虫明）などの所領を譲り受け竹原小早川家の家督を相続した。