In 1180 however Adolf defected from Henry, who thereupon drove him from Holstein. Adolf attached himself to Frederick Barbarossa (Emperor Frederick I), with whose help he regained his lordship in 1181 after the fall of Henry. In 1188 however Frederick turned down Adolf's claim to the town of Lübeck. Adolf accompanied him on the Third Crusade. In August 1190 he reached Tyre, where he left the crusading army and returned to Holstein to defend his lands against Henry the Lion, who had in the meantime returned from exile. In 1196, he went to the Holy Land for the second time for the Crusade of Henry VI, he then returned home in 1198.