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WOE
An exclamation denoting pain or displeasure. Less frequently, it occurs as a noun denoting a disaster or calamity. For example, in Revelation 9:12, following the release of the demonic locusts from the abyss and their scourge upon those who follow the Beast, John announces, “The first woe is past; two other woes are yet to come” (niv). Again, in Revelation 11:14, immediately before the seventh trumpet is sounded John writes, “The second woe has passed; the third woe is coming soon” (niv). The woes that Revelation describes are equivalent to the plagues of the OT, although somewhat more intense in that they are demonic in origin.
The Greek word is onomatapoeic: ouai (cf. the Hebrew oi and hoi). It is not necessarily a pronouncement of judgment in every case. At times it is an expression of regret or sorrow about the miserable situation that prompted the exclamation. In each case the context needs to be taken into consideration. In Matthew 11:21 (Lk 10:13) when Jesus says, “Woe to you, Korazin! Woe to you, Bethsaida!” he was reproaching the people of those cities for their unbelief. The same is true in Luke 17:2 where Jesus pronounces woe upon the one who causes another to sin: “It would be better for him to be thrown into the sea with a millstone tied around his neck” (niv). In the Lucan Sermon on the Plain, the Beatitudes are followed by four woe statements. These statements are not so much threats as they are expressions of regret or compassion.