The first part of verse 23 refers to the mission the twelve which is about to begin, the disciples are going to go through the towns of Israel. But what does it mean they will not have gone through all the towns of Israel before the Son of Man comes (v. 23b)? “This is one of the most problematic verses in the Bible” (Wilkins, Matthew, 394). There are several options for understanding this difficult verse.
First, the “towns of Israel” is an unusual way to describe the short-term mission. They are going to the towns of Galilee, but Israel as a geographical area no longer exists. Some therefore expand this to all of the Jewish communities in the Diaspora. As Nolland suggests, this is unlikely. For Nolland, Jesus’s point is the twelve will not have fled all the villages in Palestine until the Son of Man comes (Matthew, 427).
Second, when the Son of Man comes is eschatological, alluding to Daniel 7:13-14. The Son of Man is the judge of the nations and the one who initiates God’s Kingdom. Jesus calls himself the Son of Man frequently in the Gospel of Matthew (9:6, for example). Does this refer to the second coming of Jesus? At this point in Matthew, Jesus has not mentioned his death and departure, so the idea of “return” would be strange. However, he may be referring to Daniel and the Jewish expectation of the Son of Man judging the nations without yet implying anything about a departure and return. Certainly, later readers would have understood this as the “return of Jesus.”
Third, this section is remarkably similar to Matthew 24:9-14. Describing the time after the birth pains that are NOT signs of the end (24:4-8), Jesus warns his disciples of persecution and promises everyone who stands firm to the end will be save. In 24:14 he says the gospel of the kingdom will be preached in the whole world, and then the end will come. (the abomination of desolation is the next paragraph). Rather than the “towns of Israel” he says the whole world will hear the gospel of the kingdom.
Jesus and his disciples thought the kingdom of God will be fully realized in their lifetimes. This may refer to Pentecost, or a failed belief Jesus would establish the kingdom soon after Pentecost. This refers to the mission in Acts and culminates in the destruction of Jerusalem in A. D. 70. Jesus shifts from the immediate future to the distant future, as he will do in Matthew 24:4-8 (present age) and 24:9-14 (the future tribulation just before the end).
Despite rejection and persecution, there will be a continuous mission to both Israel and the Nations until the Second Coming of Jesus to establish his kingdom in the future. The twelve are not called to live a comfortable life as executive leaders, they will suffer because the maintain their testimony until the very end, even if that end results in martyrdom. The reason the disciples will suffer is their relationship with Jesus (10:24-25). Jesus has already been accused of casting out demons by the power of Beelzebul (9:34) and this will be the cause of the decisive break from the Pharisees (12:22-37).
The problem for interpreters here is “when is this?” Matthew 24:19-13 also warns about very similar persecution on account of the name of Jesus in an eschatological context; the next paragraph predicts the abomination which causes desolation (24:15-21). When the persecution happen? In the apostolic period? During church history? Only in a future “tribulation period” prior to the second coming?
The immediate application is to the Twelve and the persecution they will face as they present the Gospel to the Jews first, and eventually to the rest of the world.
There is an application for contemporary Christianity. Jesus is clear if you are representing Jesus, the world will treat you the same way they treated Jesus. There is no promise in the Gospel that the disciple of Jesus will be free from suffering, either from the typical things that happen in this world or from targeted persecution for your faith.
How does the admonition to be “wise as serpents and innocent as doves” work in the context to contemporary persecution? Maybe, “don’t hide your faith, but don’t go out of your way to get persecuted.” This seems to have been Paul’s policy.