What does Matthew 23:27 mean?
Jesus continues to pronounce judgment on Israel's religious leaders: the scribes and the Pharisees. In this next "woe" statement, He describes them as tombs that have been painted over. Under Old Testament law, anyone who came into contact with a dead body became ceremonially unclean (Numbers 19:11). The Pharisees avoided this at all costs.Despite outward appearances, these hypocrites (Matthew 23:13, 15, 23, 25) have hearts which are disgusting. In this era, the caves or rock piles used for tombs were regularly painted or washed white with lime. Some had artful memorials built over the graves. Outwardly, they look clean and neat. And yet, beneath those clean, attractive exteriors were rotting corpses. Beautiful though they may have been, they were full of death and as unclean as anything a faithful Jew could imagine.
In the same way, the Pharisees appeared to be the most unstained of all the Israelites. Inwardly, though, Jesus describes them as full of death. In this way, they are like the cups Jesus described in the previous "woe"--clean on the outside and filthy inside (Mathew 23:26).