A brahmin, chief minister of Ajátasattu. He and Sunidha were in charge of the fortifications of Pátaligáma, built against the Vajjí. (Vin.i.228; Ud.viii.6; the Dígha account, D.ii.72ff. omits Sunidha. The Vinaya account omits Vassakára’s questions to the Buddha; cf. AA.ii.705ff).
At Ajátasattu's suggestion, Vassakára visited the Buddha to discover, indirectly, whether, in the Buddha's view, there were any chances of Ajátasattu 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 Sárandada cetiya, they would prosper rather than decline, and this gave Vassakára the idea that the downfall of the Vajjians could be brought about by diplomacy (upalápana) 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. Vassakára 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. Vassakára then sent a message to Ajátasattu, who was able to capture Vesáli without meeting any resistance.
In the Gopaka Moggallána Sutta (M.iii.8ff), Vassakára is represented as arriving in the middle of a conversation, which Gopaka Moggallána was holding with Ananda, having been sent to inspect the works at Rájagaha, which were in charge of Moggallána. 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. Vassakára admits this as good, as does also Upananda, the Senápati, who is present. Vassakára asks Ananda where he lives, and is told, in Veluvana. Vassakára thinks this a good place for the practice of jhána, and tells Ananda of a conversation he once had with the Buddha regarding jhána. Ananda, remarks that all jhánas are not equally praiseworthy, and Vassakára takes his leave.
Buddhaghosa says (MA.ii.854) that Vassakára 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. Vassakára once saw Mahá Kaccána descending Gijjhakúta and remarked that he was just like a monkey. The Buddha, hearing of this, said that, unless Vassakára begged the Elder's forgiveness, he would be born as a monkey in Veluvana. Vassakára, 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 Vassakára.
Three conversations between the Buddha and Vassakára are recorded in the Anguttara Nikáya, all three taking place at Veluvana. See Vassakára Suttas (1) and (2), and Suta Sutta ??. Another Sutta, also called Vassakára (3), repeats the conversation recorded in the Dígha regarding the possibility of Ajátasattu defeating the Vajjians.
Vassakára 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. Vassakára 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 Vassakára 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 Vassakára was Mahámatta (? prime minister) to Bimbisára as well.