I fully agree the Rich Man represents the Jews...but Lazarus doesn't represent any Jew, but Gentiles. How?
If you remember that time when Jesus went up North, there was a Syro-Phoenician woman there that begged Him to heal her daughter...and finally, when Jesus said, "It's not meet (appropriate) to take the children's bread and cast it to dogs" the woman replied, "Truth, Lord...yet the DOGS eat of the CRUMBS that fall from their master's TABLE". Both Jesus and the woman knew exactly what she meant. She was saying, "Yes, Lord, I know the Jews are the masters...I know they sit at Your table of blessing, but in their hardness against You, they're allowing Your blessings to fall off the table, and though I'm a Gentile cut off from the blessings of God, I can eat the ones that fall off the table!"
While the Jews were "rich" in the promises, the covenants, the blessings, the lively oracles of God, Lazarus is said to be "outside" the gate, laying "full of sores" with the "dogs" and desiring the "crumbs" which fall from the Rich Man's "table". Yet, Lazarus winds up being "comforted" in Abraham's bosom.
This parable is yet another of several parables of warning to the Jews that if they don't repent, the tables will be turned on them....and that's exactly what happened. When they crucified Jesus and continued to oppose Christianity, finally God raised up Paul to carry the "Gospel to the Gentiles" where the Gentiles recieved all the Promises, the New Covenant, the New Testament, and the COMFORTER aka the Holy Ghost.
Some argue, "It can't be a parable because it contains the proper names "Lazarus" and "Abraham" - however, this argument is based purely in inference, not the evidence of Scripture. There is no Biblical prohibition against doing such. "Abraham" is used to establish the relationship Gentiles now have as "heirs" of Abrahams's promise (Galatians 3:29 KJV) and "Lazarus" is used so that in a short while after when the real Lazarus was raised from the dead and the Jews not only failed to repent, but went away to "take counsel on how they might destroy both Jesus and Lazarus" then the final words of this parable would ring true: "if they believe not Moses and the Prophets (aka Word of God) they will not believe, though one rose from the dead".
What say you, friend?
Here is a explanation which makes sense, by Larry Wilson in Wake Up America which really unpacks what the parable was about...
"The words of Jesus are deep and sometimes difficult to understand. He is called "The Word of God" in Scripture for good reason. His ability to put spiritual concepts into words has no equal. So, let us review the story from Scripture and then I will try to explain it: "There was a rich man who was dressed in purple and fine linen and lived in luxury every day. At his gate was laid a beggar named Lazarus, covered with sores and longing to eat what fell from the rich man’s table. Even the dogs came and licked his sores. The time came when the beggar died and the angels carried him to Abraham’s side. The rich man also died and was buried. In hell, where he was in torment, he looked up and saw Abraham far away, with Lazarus by his side. So he called to him, ‘Father Abraham, have pity on me and send Lazarus to dip the tip of his finger in water and cool my tongue, because I am in agony in this fire.’ But Abraham replied, ‘Son, remember that in your lifetime you received your good things, while Lazarus received bad things, but now he is comforted here and you are in agony. And besides all this, between us and you a great chasm has been fixed, so that those who want to go from here to you cannot, nor can anyone cross over from there to us.’ He answered, ‘Then I beg you, father, send Lazarus to my father’s house, for I have five brothers. Let him warn them, so that they will not also come to this place of torment.’ Abraham replied, ‘They have Moses and the Prophets; let them listen to them.’ ‘No, father Abraham,’ he said, ‘but if someone from the dead goes to them, they will repent.’ He said to him, ‘If they do not listen to Moses and the Prophets, they will not be convinced even if someone rises from the dead.’" (Luke 16:19-31)
The first thing I like to do after reading any passage from Scripture is to ask myself a few questions. What is the setting of this passage? Who is talking to whom and under what circumstances? Is there a contest or conflict going on? In this particular story, who is the beggar named Lazarus? Who is the rich man who had five brothers? Were both people identifiable to the listeners? What effect was this story supposed to have upon the listeners? What did the listeners know then that we need to know now so that we can properly frame and understand the story? Ultimately, what is the focal point of the story? With these questions in mind, please consider the following:
Jesus told the story of the rich man and Lazarus in the presence of His disciples and a group of scoffing Pharisees. (Luke 16:14) He created this illustration because the Pharisees refused to believe anything that He said. They had seen many miracles and they still refused to believe He was the Messiah, so Jesus gave them a prophecy in the form of a story. As the story unfolds, Lazarus and the rich man die and their eternal rewards shock the listeners. The rich man goes to hell and the beggar goes to Abraham’s side. This was the exact opposite of what the listeners expected. Jesus did not confront the Pharisees with loud words nor did He engage them with 100 proof texts from the Old Testament proving that He was the Messiah. Rather, Jesus created a small bomb which He planted in their minds. The story would be memorable because well known people were used and the destiny of both was totally different than what the listeners expected. It is possible the Pharisees found this story a bit amusing at first, but the story probably made them angry once they figured out its meaning. So, Jesus created a story that begins with Middle East intrigue and it ends with a condemning knockout punch.
Errant Theology
Unlike the Sadducees, the Pharisees believed in a hereafter. They believed in eternal life and an eternally burning hell. They also believed that blessings and prosperity came from God as a reward for rigorous obedience to the law. (Philippians 3:6, Deuteronomy 28:1-14) One of their favorite texts was, "Keep my decrees and laws, for the man who obeys them will live by them. I am the Lord." (Leviticus 18:5) The Pharisees also believed that poverty and illness were the results of sinning against God. "Cursed is the man who does not uphold the words of this law by carrying them out. . . ." (Deuteronomy 27:26; 28:15-68) So lepers, beggars and poor people deserved to suffer. Simply stated, such people were under a curse because either they or their parents had sinned against God. (See John 9:2.) Since most Christians are not well informed on the Pharisees’ beliefs, they just read how Lazarus went to Abraham’s side and the high priest went to hell as though that was the way it should have been. Not so! The Pharisees believed just the opposite and this conflict in the story puzzled them.
Simon Lazarus
There is only one person in the Bible having the name Lazarus. He lived in Bethany. Most Christians have heard of him because he was the brother of Mary Magdalene and Martha. But many Christians do not know that Lazarus had a first name! His full name was Simon Lazarus and he was a leper. (John 12:1-3; Matthew 26:6) Jesus knew that His listeners were acquainted with Lazarus’ leprosy and this illness explains the presence of his sores in the story. Lazarus was reduced to a position of begging when he became leprous and the Pharisees had no sympathy. They regarded him as one condemned by God – a cursed sinner. (Note: Mary Magdalene, Lazarus’ sister, was the prostitute who Jesus rescued from stoning. (John 8:3-11) Whether she turned to prostitution to provide for herself, her brother and sister after Lazarus contracted leprosy is not known.)
Caiaphas
Jesus could not speak the name of the rich man with five brothers for a simple reason. It would have been considered blasphemy by the Pharisees to say anything less than honorable about him. (John 18:22) Nevertheless, everyone present knew who the rich man was because he wore purple and fine linen every day (an elegant robe), he lived large (spent a lot of money) and fared sumptiously (ate too much), and he was Israel’s religious leader. The rich man who had five brothers was the high priest of Israel, Caiaphus.
As a young man, Caiaphus married into a family of high priests. (John 18:13) Thus, Caiaphas became a son-in-law of Annas (a former high priest) and Caiaphas served as high priest in Jerusalem between A.D. 18 and A.D. 35. Because of marriage, Caiaphas had five brothers-in-law and each of these men eventually served terms as high priest in Jerusalem. Josephus wrote, "Now the report goes, that this elder Ananus proved a most fortunate man; for he had five sons, who had all performed the office of a high priest to God, and he had himself enjoyed that dignity a long time formerly, which had never happened to any other of our high priests. . . ." (Antiquities, book XX, chapter IX, paragraph 1, p.423, Kregel Publications, Grand Rapids, Michigan, 12th printing, 1974) Their names and years of service follow: Eleazar A.D. 16-17; Jonathan A.D. 36-37; Theophilus A.D. 37-41; Matthias A.D.41-43; Annas the Younger A.D. 62.....