After teaching his disciples the Parable of the Unjust Steward, and then rebuking the Pharisees for their ill treatment of the word of God, Jesus told a story about a rich man and a beggar named Lazarus (Luke 16:19-20). The rich man was clothed in purple and fine linen, and this should remind us of the clothing of the high priest (Exodus 23:4-6). So, Jesus is probably still teaching about the same people he alluded to in the Parable of the Unjust Steward (Luke 16:1-13).
I believe Jesus may be contrasting the rich man in this story (Luke 16:19) with the rich man in the Parable of the Unjust Steward (Luke 16:1). Moreover, because the unjust steward made disciples of the rich man’s debtors in the parable (Luke 16:4-7), it may be that the rich man in Jesus’ present story (Luke 16:19 and following) is the unjust steward in the parable at the beginning of Luke 16. That is, the unjust steward of the parable mentioned in Luke 16:1 became a rich man in his own right, because of the manner in which he made disciples of the first rich man’s debtors.
Luke doesn’t tell us that Jesus is speaking another parable in Luke 16:19-31, so we shouldn’t be too quick in assuming he is doing so. In fact, it would appear that Jesus is repeating a rabbinic story rather than a parable. That is, Jesus is using an existing rabbinic argument for the sake of the Kingdom of God. The fact is, the logic of this story had been used by the Jewish authorities to benefit their own worldview. Jesus did something similar near the beginning of his ministry, when he told a man with palsy that his sins were forgiven. Not everyone who is sick or debilitated inherited their condition, through sinfulness. Yet, Jesus used this point that was taught by the rabbis and Pharisees to make his own point about his being the Messiah (cf. Luke 5:20-25).
Moreover, we have a similar case in Luke 20:27-33 where the Sadducees came to Jesus with a question. There, they thought to debunk Jesus’ argument about a resurrection by showing how incongruous a resurrection worldview could be, and they tried to do so through a clever story. Nevertheless, Jesus used their own words against them, but adding Scripture to show there was, indeed, a resurrection (Luke 20:34-38). That Luke 16:19-31 is, indeed, a rabbinic story and not a parable seems certain, because of what Jesus says in Luke 16:22 and 30. Notice that Luke 16:22 says the beggar was carried to Abraham’s bosom. ‘Abraham’s bosom’ was a rabbinic hope, not the Christian hope (Ephesians 2:12; Titus 1:1; 2:13; 1Peter 1:13). The Christian hope is to be found in Christ. Additionally, it seems this particular rabbinic story was formed as an argument against the resurrection (Luke 16:30). That is, it was an argument by the Sadducees against the Pharisaical worldview, but it is used by Jesus to support his doctrine of the resurrection as understood in the Gospel.
The implied argument in the story seems to be: “certainly, a fair God, a just God, a loving God would do everything possible to keep his people out of a place of torment. Certainly, such a God would understand that causing Lazarus to rise from the dead would turn the rich man’s relatives around. Certainly, they would repent, if they witnessed a resurrection, and they would then believe.” Thus, the theme or worldview that the rabbinic story presents is not only one against the Gospel of the Kingdom of God in general, but also against the resurrection in particular.
In Luke 16:17 Jesus made the argument that since by the word of God the heavens and the earth were brought into existence, it stands to reason that it would be easier for the heavens and the earth to pass away than for the least part of the word of God to fail. That is, God’s word is more real than what we see as our reality. Therefore, Jesus says, if the rich man’s five brethren wouldn’t hear Moses and the prophets (i.e. if they don’t consider the word of God proof enough), how could they repent, if they simply saw a man return from the dead? Thus, Jesus rendered the rich man’s argument moot.