ESV - 17 And alas for women who are pregnant and for those who are nursing infants in those days!
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Jesus' emphasis in these verses is on the speed that will be required to escape, if possible, the devastation that He is indicating will occur in the days to which He is referring. Under those circumstances, the hindrance to such speed that would be created for a woman either by being pregnant, or by still nursing a child who is not yet old enough to be independent of her, might mean the difference between being able to escape or not. The possible climate conditions present during winter weather, as well as the shorter daylight hours, would present a similar impediment. Also, for Jewish Christians (the audience to whom Matthew was primarily addressing his gospel) restrictions contained in the Law on the distance that could be traveled on the Sabbath, or the closing of gates and other possible escape routes that might occur because of the Sabbath, would create problems. (Mark, who wrote his gospel primarily for a Roman readership, did not include this aspect in his account of Jesus' words, since it would have had no meaning to Gentiles.)
Reading Matthew 24:20 it’s easy to see why fleeing while pregnant or in the winter would be less than desirable. Being homeless is never easy, but it's especially hard when the weather is unpredictable and you are expecting a baby. However, why Jesus is telling them to pray that their flight is not on the Sabbath? After all, Jesus here is referring to the fall of Jerusalem in AD 70, almost 40 years after his resurrection. If we believe that with Jesus’ death, the Fourth Commandant was done away, the 7th-day Sabbath is no longer holy, and Sunday is now the new Sabbath, in honor of His resurrection - Jesus' warning would make no sense. Was Jesus still concerned with keeping the Sabbath day holy 40 years after His death? I strongly believe that Jesus mentioned the Sabbath because its relevancy, importance and sanctity still mattered to Him, even 40 years after His resurrection. The reason for its importance is the same as it was in the beginning (Gen 2:3) - a reason for keeping the Sabbath day a holy assembly to celebrate and worship the creator of “heaven, the earth and the sea” (Ex 20:11). However, citing Nehemiah 13:19, some Bible commentators believe the reason why Jesus mentioned the Sabbath is because the gates of city would be closed thus making the escape difficult or even impossible. That's a problematic proposition as Jesus here makes an appeal not only to the people inside the city walls but also to “those who are in Judea” (Matt 24:16) who were outside the city gates – thus the city gates being closed or not is not relevant. Additionally, according with Josephus, a Jewish historian, the Jerusalem gates were not closed or guarded at the time Christians fled the city – looking 40 years into the future Jesus would have known that little detail. The army of Cestius Gallus enclosed Jerusalem in A D 67, then suddenly withdrew to Cæsarea. The Jews left the city in pursuit, which in turn gave the Christians the opportunity to flee beyond the Jordan. God made a way for them to flee on a Tuesday, in October – their flight was neither in the winter, nor on the Sabbath day. The Roman armies returned and on August 10, AD 70, the city was stormed and over one million people were killed, and 100 000 survivors were taken into slavery.
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