Daijiji was first dispatched to Ryûkyû in 1589 after a letter from Toyotomi Hideyoshi (dated 1589/1/17) ordered the Shimazu to suppress pirate activity and to work to restore formal trade relations with the Ming Empire; the letter threatened the destruction of the Shimazu clan and military action taken against the Ryûkyû Kingdom if Shimazu Yoshihisa were not to take action.
After arriving in Ryûkyû, Daijiji then escorted Ryukyuan envoys Chôan and Adaniya peechin back to Kagoshima and then to Osaka for audiences with Hideyoshi himself. A letter given to the embassy by Hideyoshi, and another sent to Ryûkyû via the Shimazu after the embassy's return, ordered Ryûkyû to contribute to Hideyoshi's upcoming attempt to invade China and Korea, and to send a formal diplomatic embassy (ayabune) to present Hideyoshi with gifts and respects.
Daijiji returned to Ryûkyû again nearly two decades later, in 1608/8, acting as an envoy of the Shimazu and seeking Ryûkyû's official submission to Shimazu and Tokugawa authority. The shogun formally granted the Shimazu permission to invade Ryûkyû the following month.
- Gregory Smits, Maritime Ryukyu, University of Hawaii Press (2019), 213-214.