Just as the religious people had murdered God's spokespeople in the past (vv. 29-31), they would do to Jesus (v. 32) and his followers (v. 34). But whatever judgments past generations might have suffered, the true guilt had been saved up for the climactic murder of this generation—the execution of Jesus (27:25). Like Matthew 24, this section views the destruction of the temple, due to occur in the leaders' generation (23:35-38), in the context of the final period of judgment (vv. 33, 39).

John the Baptist had demanded to know who warned these offspring of vipers (see comment on 3:7; compare 12:34) to flee approaching hellfire yet failed to call them to bear fruits of repentance (3:7-8). Jesus offers the same message (23:33). The prophets, wise men (hokmim, "sages") and teachers ("scribes") Jesus would send represent the various missions of his own followers (5:12; 13:52; compare "apostles" in Lk 11:49), whether they came as prophetic or teaching figures (see 11:18-19). Jesus here fills a role that God filled in the biblical tradition (as in 2 Chron 36:15-16). These prophets, like the earlier prophets Jesus mentioned (Mt 23:29-31; compare 21:35-36) and himself (23:32, 36; compare 21:39), would face persecution (see again 10:17, 23).

Filling up the cup to the brim refers to meriting all the blood (bloodguilt) saved up among past generations, never punished as was deserved (compare Deut 32:43; Ps 79:10; Is 40:2; Rev 6:10). The blood of Abel, a prototypical martyr (as in Ps-Philo 16:2), had cried for vengeance against his fraternal slayer (Gen 4:10; Heb 11:4; 12:24; Jub. 4:3; 1 Enoch 22:6-7). Jesus' second example is probably the Zechariah of 2 Chronicles 24:20-22, martyred in the temple. According to Jewish tradition, Zechariah's blood, like Abel's, cried against the murderers for vengeance, yielding the massacre of many priests (b. Gittin 57b; p. Ta`anit 4:5, Section 14; Pes. Rab Kah. 15:7). The bloodguilt for Jesus' death would fall on that generation (Mt 27:25). And as Zechariah's blood had once desecrated the priestly sanctuary and so invited judgment (Lives of Prophets 23:1; Sipra Behuq. pq. 6.267.2.1), so would the blood of the priests in A.D. 66 as the "abomination that causes desolation" (24:15).