Career
Originally a retainer of Nagahide Niwa, Masaie as a fi.nancial adviser of his master ably helped him to amass a huge fortune. Hideyoshi Toyotomi, upon hearing this, accorded him a fief of 10,000 koku and entrusted with him the task of handling tributary payments, tax and accounting business of his feuds. Masaio thenceforth rose successively in rank and ultimately became Okura Tayu (Vice-Minister of Finance) with the title of Ju-goi or Junior Grade of the 5th Court Rank and was made castellan of Minakuchi Castle in the province of Omi (Shiga Prefecture) with a fief of 50,000 kcku. When Hideyoshi led an expedition against the Hojo family at Odawara it was Masaie who was in charge of matters con¬cerning provisions and transportation of the troops (1590). After the death of Hi¬deyoshi, Masaie tried to curry favor with Ieyasu Tokugawa by informing mm jninutely on the doings of Mitsunari lshida. The popular belief that Masaie was nothing but an unrefined sneak may be attributed to the fact that he during all this time secretly maintained contact with Mitsunari lshida himself and soon exposed his real self by attacking Anotsu Castle with Morichika Chosogabe and others and settled himself at Ogkki where he joined the ranks of Mitsunari lshida. Later he fought under Mitsunari at the Battle of Sekigahara and then after a bitter defeat and a narrow escape from death fled back to his old home at Minakuchi. He, however, was soon overtaken by the oncoming army of Terumasa Ikeda and his younger brother Nagatsuka Chokichi and was forced to commit suicide with Iganokami Nagatsuka, his son.
