What does Luke 16:23 mean?

The rich man finds himself in a state of damnation. He had lived a luxurious lifestyle with expensive clothing and rich foods. Outside his gate, a beggar named Lazarus lay, futilely begging for the scraps from the rich man's table. Lazarus was starving, covered in sores instead of purple robes, and likely crippled. The only thing the two had in common is they both died.

Hades is a general term for the place of the dead, although some Jewish literature gives a different name for the dwelling of God-following Jews. This causes continued confusion as Acts 2:27 infers Jesus went to Hades when He died, leading some to believe He spent three days in hell. Whether Lazarus' paradise is in a section of Hades, we don't know. We just know that Lazarus is in paradise and the rich man is in torment. From his place in Hades, the rich man can see Lazarus being welcomed by Abraham (Genesis 12:1–2). The rich man seems to know why he didn't qualify, and he doesn't argue why he's in torment.

The difference between their stations in life is exaggerated in death. Jesus promised this to His disciples: they had the kingdom of God, even if poor then; their hunger would be satisfied (Luke 6:20–21). He pronounced woe to those who were rich: this world is their consolation if they depend on riches; though they were full, they would be hungry (Luke 6:24–25). That doesn't mean, of course, that all people who are poor on earth will be saved and every rich person will go to hell. In the context of Luke 16, what people do with their money strongly indicates if they follow God or not.

The imagery reflects Jewish tradition, not necessarily reality. Extra-biblical Jewish books claim those in paradise and those in Hades can see each other. Jesus does warn that unbelieving Jews will be able to see "Abraham and Isaac and Jacob and all the prophets in the kingdom of God" when they are cast out (Luke 13:28).