Masamune had kept the alliance with Gohojo clan formed by his father, Terumune DATE, thus he was irresolute until the last moment whether he should fight against Hideyoshi, or join the Odawara Attack (the war led by Hideyoshi Toyotomi and his allies against Hojo clan).
政宗は父、伊達輝宗の時代から後北条氏と同盟関係にあったため、秀吉と戦うべきか小田原に参陣すべきか、直前まで迷っていた。