A brahmin, chief minister of Ajātasattu. He and Sunidha were in charge of the fortifications of Pātaligāma, built against the Vajjī. (Vin.i.228; Ud.viii.6; the Dīgha account, D.ii.72ff. omits Sunidha. The Vinaya account omits Vassakāra’s questions to the Buddha; cf. AA.ii.705ff).
At Ajātasattu's suggestion, Vassakāra visited the Buddha to discover, indirectly, whether, in the Buddha's view, there were any chances of Ajātasattu conquering the Vajjians in battle. The Buddha said that as long as the Vajjians practised the seven conditions of prosperity which he had taught them at Sārandada cetiya, they would prosper rather than decline, and this gave Vassakāra the idea that the downfall of the Vajjians could be brought about by diplomacy (upalāpana) or disunion (mithubheda). He thereupon conspired with the king (D.A.ii.522ff ) and, by agreement, the latter expelled him on the charge of showing favour to the Vajjians during discussions in the assembly. Vassakāra then went to the Vajjian country, and the Licchavis, all unsuspecting, welcomed him and appointed him as the teacher of their children. By means of cunning and questioning the children in secret, he made them quarrel with each other, and these quarrels soon spread to the elders. In three years the Licchavis were completely disunited, and when the assembly drum was beaten, they failed to appear. Vassakāra then sent a message to Ajātasattu, who was able to capture Vesāli without meeting any resistance.
In the Gopaka Moggallāna Sutta (M.iii.8ff), Vassakāra is represented as arriving in the middle of a conversation, which Gopaka Moggallāna was holding with Ananda, having been sent to inspect the works at Rājagaha, which were in charge of Moggallāna. Having asked the subject of conversation, he inquired whether the Buddha himself or the Order had chosen a leader for the Sangha after the Buddha's death. Ananda explains that the Buddha did not do so, that no special leader has been appointed, but that there were monks to whom they showed honour and reverence because of their virtue and insight. Vassakāra admits this as good, as does also Upananda, the Senāpati, who is present. Vassakāra asks Ananda where he lives, and is told, in Veluvana. Vassakāra thinks this a good place for the practice of jhāna, and tells Ananda of a conversation he once had with the Buddha regarding jhāna. Ananda, remarks that all jhānas are not equally praiseworthy, and Vassakāra takes his leave.
Buddhaghosa says (MA.ii.854) that Vassakāra knew well of Ananda's residence at Veluvana, but that as the place was under his special protection, he wished to hear his work praised. Then follows a curious tale. Vassakāra once saw Mahā Kaccāna descending Gijjhakūta and remarked that he was just like a monkey. The Buddha, hearing of this, said that, unless Vassakāra begged the Elder's forgiveness, he would be born as a monkey in Veluvana. Vassakāra, feeling sure that the Buddha's prophecy would come true, had various fruit and other trees planted in Veluvana, to be of use to him as a monkey. After death he was actually reborn as a monkey and answered to the name of Vassakāra.
Three conversations between the Buddha and Vassakāra are recorded in the Anguttara Nikāya, all three taking place at Veluvana. See Vassakāra Suttas (1) and (2), and Suta Sutta ??. Another Sutta, also called Vassakāra (3), repeats the conversation recorded in the Dīgha regarding the possibility of Ajātasattu defeating the Vajjians.
Vassakāra had a daughter whom he wished to give in marriage to Uttara, but the latter refused the proposal as he wished to join the Order. Vassakāra was angry, and contrived to take his revenge even after Uttara had become a monk (ThagA.i.240; see Uttara).
Buddhaghosa says (Sp.ii.295) that Vassakāra was envious by nature, and, on discovering that a certain forest official had given tribute to Dhaniya (2) without the king's special leave, he reported the man to the king and had him punished (The incident is repeated at Vin.iii.42ff). In this context we find that Vassakāra was Mahāmatta (? prime minister) to Bimbisāra as well.