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In Matt 23:27, Jesus equates Sadducees and Pharisees to whitewashed tombs. Before the advent of long- lasting tombstones , the tombs , mostly formed of mud, used to be whitewashed and decorated with flowers on special occasions . Poor families which cannot afford to pay for permanent tombs, still have the tombs of their dear ones whitewashed, in many countries. That the practice was prevalent at Jesus' time indicates that Jews had been following it since long. My question therefore, is: Are there any instruction in the OT, which deal with maintenance of tombs, especially whitewashing ?

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I am not aware of any stipulation for tomb decorations within the Mosaic law.

If we take a similar versus from Luke 11:44 this might help,

“Woe to you [Pharisees], because you are like unmarked graves, which people walk over without knowing it.”

I believe the rationale is an extension of Numbers 19:11-13:

11 "Whoever touches the dead body of anyone will be unclean for seven days. 12 He must purify himself with the water on the third day and on the seventh day; then he will be clean. But if he does not purify himself on the third and seventh days, he will not be clean. 13 Whoever touches the dead body of anyone and fails to purify himself defiles the LORD's tabernacle. That person must be cut off from Israel.

The penalty is severe cut off from Israel. Therefore, accidentally touching the tombstones could represent some form of touching the deceased. It could also be they physically touch the deceased if the tomb collapses and would be problem in the Mosaic law. Given the nature of the penalty it is better to alert everyone to the presence of a tomb, by whitewashing it.

In your context the idea is that the dead body is unclean, whether it is a skeleton or recently deceased individual. This was analogous to the Pharisees being beautiful tombs. They probably looked fantastic and kept impeccable ritual. However, they would ultimately pay blood-money for Jesus betrayal, then get a man convicted of murder spared the death penalty for the singular purpose of a massive miscarriage of justice by crucifying Jesus, who was the number 1 threat to their power-base.

I would suggest their behaviour was a violation of at least 3 of the 10 commandments, "Do not murder", "Do not give false testimony", "Do not covert". Therefore, they were like dead bodies in a beautified tomb.

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