There are several causes for weeping recorded in the New Testament. Matthew's Gospel records six times in Jesus' teaching in which he warned about the people who, when finding themselves separated from God eternally, would wail and gnash their teeth in anger or despair (Matt. 8:12-13; 13:42,50; 22:13; 24:51; 25:30).
Then there is the case of Peter, when realizing that he had denied his Lord as Jesus predicted, cried with bitter regret for what he had done. Or on the other end of the spectrum were the more or less professional mourners at the respective death beds of Jairus' daughter (Luke 8:52-53) and Lazarus (Mark 5:39-40) who somehow managed to instantly turn their crocodile tears to derisive sneers at Jesus when he told them that there was nothing to mourn about. Altogether there are approximately 35 verses in the Gospels in which people cry.
But then we come to the specific case of Jesus himself weeping. I have already discussed one of the two instances in which we are told that this happened (see the post titled “Jesus Wept.” [John 11:35]). On that occasion it was the death of his friend Lazarus which triggered that emotional response. But in Luke 19:41, it was the city of Jerusalem which Jesus was weeping over as he anticipated the fate she would soon experience.
Tilden cites Luke 13:33-34 in conjunction with this verse. In this parallel passage Jesus bewails the fact that He had wished to gather its inhabitants under His wing but instead they rejected Him. This same reason is given for his sadness in chapter 19, which goes on to say that they would be experiencing grief “because you did not know the time of your visitation” (v. 44).
This may be an allusion to an earlier episode in Luke's Gospel, as Porter states: “Zechariah the priest (1:67-68) had praised God who had visited His people; You, says Jesus to the people of Jerusalem, you did not recognize the time of God's coming to you.”
Vine defines the particular Greek verb for “cry” in these verses: “klaio is used of any loud expression of grief, especially in mourning for the dead.” Of course, that definition also fits in Luke 13, even if the ones mourned for are not yet dead, but doomed to die not only physically but also spiritually and eternally.
The anonymous footnote in the Jerusalem Bible points out: “This whole prophecy is made up of O.T. references (especially noticeable in the Greek text for v. 43, cf. Is 29:3; 37:33; Jr 52:4-5; Ezk 4:1-3; 21:27; for v. 44, cf. Ho 10:14; 14:1; Na 3:10; Ps 137:9)...” That commentator feels that it applies to the destruction of Jerusalem back in 587 B.C. even more than the Roman destruction of 70 A.D.
Others scholars are suspicious of Jesus' words as an actual prophecy, as Fitzmyer explains. He first notes that “the unusual syntax reveals that Luke is making use of an inherited piece of tradition, which he has only slightly redacted...This passage has been classed by R. Bultmann as a biographical apophthegm, i.e. a pronouncement-story, not an 'imaginary scene,' even though the pronouncement itself is regarded by him as a vaticinium ex eventu [i.e. prophecy after the event], fitted out with an introductory setting in v. 41...Others have ascribed the predictions to early Christian prophets and claimed that they were eventually attributed to Jesus in the pre-Lucan tradition...the interest in the episode lies not in Jesus' weeping, but in the pronouncement that he utters...Is the utterance to be simply dismissed as vaticinium ex eventu? The question is complicated because it is involved in the dating of the Lucan Gospel and because vv. 43-44 are echoes of OT minatory [expressing a threat] predictions. Yet a number of commentators are reluctant to deny that the utterance goes back to Jesus himself in some form...There is, indeed, reason to think that Jesus did actually say something similar to this prophetic pronouncement about the fate of Jerusalem or at least of its Temple.” In addition, Fitzmyer asks the good question: “Would not a vaticinium ex eventu have been more specific in its terminology?”
He also notes, “Another opinion is held by C. H. Dodd who maintains that this oracle of the Lucan Jesus is 'composed entirely from the language of the Old Testament...So far as any historical event has colored the picture, it is not Titus's capture of Jerusalem A.D. 70, but Nebuchadrezzar's capture in 586 B.C.'...Fitzmyer concludes that “the best solution to this problems is the recognition that the Lucan oracle may well go back to Jesus in some form, but that the reformulation of it in the pre-Lucan tradition was affected both by the destruction of the city itself in A.D. 70 and by allusions to that under Nebuchadnezzar in the OT.” As you will see in the following description of the events by more conservative scholars, they are not nearly as skeptical regarding the true prophetic nature of Jesus' pronouncement but take it for granted that Luke's words reflect an accurate historical recollection of the facts.
Ellis says, “It is sometimes argued that the prophecy could not have originated in the pre-resurrection mission because Jesus anticipated the destruction of Jerusalem only as an eschatological, i.e., end of the world, event.” But he concludes, 'there are no good grounds to disallow the oracle to the pre-resurrection mission...”
“There is a sudden change of tone as Jesus turns to look at the city spread before Him and utters a sorrowful prophecy about its fate. He longed that even at this late stage it might repent and seek what would be for its welfare: how little did the conduct of Jerusalem, the city of peace (Heb. 7:2), resemble its name.” (Marshall)
“Jesus' death is both consequence of of the city's rejection of him and foretaste of what the city itself will face.” (Walton)
“In another tradition unique to Luke Jesus pauses to weep over Jerusalem as he anticipates its siege and destruction (Lk 19:42-44).” (Olmstead)
“Luke makes explicit both that certain of Jesus' prophecies refer to the imminent siege and destruction of Jerusalem (Lk 19:41-44; 21:20-24) and that there must be an interim period of 'the times of the Gentiles' before the ultimate end (Lk 21:24).” (Pitre)
Luke omits Mark's materials linking prayer and discipleship where Jesus exhorts the disciples about prayer and exorcism...and curses the fig tree..., replacing this symbol of judgment with Jesus' prophetic lament over Jerusalem (Lk 19:41-44).” (Crump)
Oakes notes that “astonishingly, in the midst of all this celebration Jesus starts weeping. He weeps that Jerusalem will not share in the peace that is coming because the people have not understood the way to peace (Lk 19:41-42). Instead, the city's enemies will encircle it, lay siege to it and tear it down (19:43-45). E. Franklin argues that this 'suggests knowledge of the Roman destruction of Jerusalem in 70 CE. Rejection of Jesus and his way of peace leads them into confrontation with Rome with its inevitable disastrous results...The specific language here [i.e. Luke 21:20] and in Luke 19:41-44 has a strong OT background in a range of prophetic versions of God's judgment on various cities (e.g. cf. Lk 19:44 with Is 3:26; Nah 3:10). J. Noland argues that 'All of God's acts of judgment and threats of judgment, as recorded in Scripture, come to their culmination in the prospect of judgment held forth here.'”
Schellenberg states that “the good news of peace that Luke attributes to Jesus cannot be relegated to the spiritual realm. Indeed, for Luke, Jerusalem's failure to recognize 'the things that make for peace' results in concrete violence: a brutal and destructive siege (Lk 19:41-44). So, although the proclamation of God's kingdom includes no summons to revolution, the enactment of the kingdom has profound social and political implications that do indeed challenge the existing political order.”
At Christ's triumphal entry into Jerusalem, 'the objection of 'some of the Pharisees' (not all) as the representative voice of all those who reject Jesus' kingship (Lk 19:39-40) leads directly into its outcome: Jesus' sorrowful lament over Jerusalem's failure to recognize the visitation of the one (i.e. God [cf. Jer 6:15]) who could bring it peace (cf. Zech 9:10), and hence its coming coming destruction (Lk 19:41-44; cf. Lk 13:34-35).” (Watts)
Lastly, below are three opinions from three anonymous scholars writing in The Dictionary of Biblical Imagery:
We should not “overlook that Jesus is arrested, tried and sentenced to execution in a city that he had characterized as 'killing the prophets and stoning those who are sent to you.' Yet even in uttering that accusation, Jesus is pictured as weeping over this wicked city...”
“Christ's tears of compassion for this people are foreshadowed in the OT by those of Jeremiah, both in his prophecy (Jer 9:1; 13:17; 14:17) and in the Book of Lamentations ascribed to him (Lam 2:11; 3:48-49). Paul is a follower of Christ in this respect, moved to tears by the strength of his caring for his converts, whether in person (Acts 20:31) or in writing (2 Cor 2:4).”
“Weeping is an expression of sorrow, a reaction to being wronged or to having committed a wrong, or to the experience of loss...Weeping is regularly associated with the plight of Israel or Jerusalem (judgment and exile). Thus Jesus' weeping in Luke 19:41 (cf. Lk 23:28, also probably referring to the coming judgment on Jerusalem) is all the more poignant as the christological culmination of this motif. The city did not recognize the time of God's visitation (in Jesus) and now faces certain and irrevocable judgment.”