A "woe" is a "condition of deep suffering from misfortune, affliction, or grief".
Because of the disobedience of the Jewish people and the religious leaders Jesus lowers the boom against them.
Consider Leviticus 26, we see a clear warning God gives the Israelite's. The Lord says, "I will punish you with terrible woes" for refusing to obey His Commandments and breaking the Covenant.

Verse 18, "...I will increase the chastisement for your sins sevenfold, to break your haughty confidence"
Verse 21, "...I will multiply my blows another sevenfold, as your sins deserve."
Verse 25, "I will make the sword, the avenger of my covenant, sweep over you. Though you then huddle together in your walled cities, I will send in pestilence among you, till you are forced to surrender to the enemy."
Verse 26, "And as I cut off your supply of bread, ten women will need but one oven for baking all the bread they dole out to you in rations, not enough food to still your hunger."
Verse 28-29, "I, also, will meet you with fiery defiance and will chastise you with sevenfold fiercer punishment for your sins, till you begin to eat the flesh of your own sons and daughters."

Verse 31, "I will lay waste your cities and devastate your sanctuaries, refusing to accept your sweet-smelling offerings."
Verse 32, "So devastated will I leave the land that your very enemies who come to live there will stand aghast at the sight of it."
Those are some very important warnings that the Israelites were given and yet, they fell flat on their faces over and over again.
Because the religious leaders did not recognize the true Messiah, because the people killed the prophets of God, Jesus declares the woes of disobedience to the Scribes and Pharisees.

Verse 15, "Woe to you, scribes and Pharisees, you hypocrites. You traverse sea and land to make one convert, and when that happens you make him a child of Gehenna twice as much as yourselves."
Verse 16, "Woe to you, blind guides, who say, 'If one swears by the temple, it means nothing, but if one swears by the gold of the temple, one is obligated."
Verse 23, "Woe to you, scribes and Pharisees, you hypocrites. You pay tithes of mint and dill and cummin, and have neglected the weightier things of the law."

Verse 27, "Woe to you, scribes and Pharisees, you hypocrites. You are like whitewashed tombs, which appear beautiful on the outside, but inside are full of dead men's bones and every kind of filth."
Verse 29, "Woe to you, scribes and Pharisees, you hypocrites. You build the tombs of the prophets and adorn the memorials of the righteous, and you say, 'If we had lived in the days of our ancestors, we would not have joined them in shedding the prophets blood."
Jesus would call the Pharisees, "brood of vipers" and warns, "Amen, I say to you, all these things will come upon this generation." (Matthew 23:36)
Recall the warning God gives in Leviticus 26? Jesus states, "Jerusalem, Jerusalem, you who kill the prophets and stone those sent to you, how many times I yearned to gather your children together, as a hen gathers her young under her wings, but you were unwilling! Behold, your house will be abandoned, desolate. I tell you, you will not see me again until you say, 'Blessed is he who comes in the name of the Lord." (Matthew 23:37-39)

The Fall of Jerusalem did in fact occur as Jesus forewarned and the Jewish Historian Josephus wrote the history of this epic siege. He writes of a woman called Mary, the Daughter of Eleazar:
"My poor baby, why should I keep you alive in this world of war and famine? Even if we live till the Romans come, they will make slaves of us; and anyway, hunger will get us before slavery does; and the rebels are crueler than both. Come, be food for me, and an avenging fury to the rebels, and a tale of cold horror to the world to

The Siege of Jerusalem was total devastation and the destruction was brutal. More than a million people were killed. Many crucified.
So terrible was the plight of the Jewish people within the walls of Jerusalem. Because of Jerusalem's unfaithfulness, riding on the back of Rome, St. John would write of this in the 17th and 18th Chapter of Revelation.
Jerusalem would be the seven hill (mountain) city that would become known as the "Whore of Babylon". St. John simply spoke of Jerusalem as "The Great City", 'Where indeed their Lord was crucified.' (Rev 11:8). Because of the political ties between Jerusalem and Rome, St. John recognized the "Woman" 'represents the great city that has sovereignty over the kings of the earth." (Rev 17:18)
It is interesting that St. John is giving a play on words here. Something that he recognized from something Jesus once said, "Repay to Caesar what belongs to Caesar and to God what belongs to God." (Mark 12:17)
To St. John, obviously God is supreme and the people's refusal to accept His sovereignty lands the seven woes of Jesus and the coming destruction of Jerusalem.
Because the Jews failed in keeping the Commandments and the Covenant, St. John saw this rebellious spirit regarding this woman (representing Israel) whom God called the "harlot", the "prostitute", the "adulterous wife". (Ezekiel 16)
As a result, the Old Testament Priesthood was obliterated and the sacrifice ceased on the 9th of Av, 70 A.D. exactly as Jesus foretold.
With this behind us, are we sure that in the United States we want to turn our gaze away from the Lord?

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