Once the Romans surrounded Jerusalem, its inhabitants could still leave the city safely until the spring of A.D. 68 (Jos. War 4.377-80, 410; Lane 1974:468). Later deserters to the Romans, suspected of having swallowed jewels to escape with them, were often cut open by Syrian auxiliaries (Jos. War 5.550-52). Jesus' command to flee to the mountains (v. 16) makes good sense; Palestine's central mountain range provided a natural refuge (as in 1 Sam 23:14; Ezek 7:15-16; Jos. War 2.504).

The admonitions to leave the rooftop without entering the house (v. 17) and to leave the field without returning for one's cloak (v. 18) indicate that life matters more than even its basic necessities, which might later be replaced (compare 1 Macc 2:28). Because outside staircases led up to the flat rooftops, one could descend without entering the house to retrieve possessions (Lane 1974:470). One normally slept in one's outer garment and wore it during the cold of morning labor in the fields, but left it at the edge of the field as the day grew warmer (Anderson 1976:296). As essential as this outer cloak was, Jesus declares that running at the news of impending destruction was more urgent still.

The "woe" over the pregnant and nursing (how dreadful, v. 19) signifies the difficulty of flight and survival (Lk 23:29), implying the sorrow of losing infants in the trauma (compare 2 Baruch 10:13-15). Verse 20 also reveals foresight concerning the sabbath and winter. On the former (mentioned only by Matthew) one could not secure animals for transport. Winter's cold limited travel; even armies stopped traveling campaigns during this season (as in Jos. War 4.442; Ant. 18.262). Further, winter rains could flood the roads and bury them deep in mud (m. Ta`anit 1:3; Jeremias 1969:58); indeed, in spring 68, because the Jordan was flowing high, Gadarene fugitives were delayed in crossing and were slaughtered by the Romans (Jos. War 4.433; Lane 1974:470-71).

Although Jesus' words specifically address the fall of Jerusalem, they provide us with some important principles. Christians who remember the nature of the time ought not to be attached to worldly possessions; we should value our lives enough to flee immediately. Indeed, God may judge materialistic Western and other societies at times to turn us from our pursuit of what does not matter so we may learn to pursue what really does. Nor ought we to believe false prophets of peace proclaiming that judgment will never strike our own locality (for example, Jer 6:14); rather than sparing a locality, God sometimes warns his servants to leave (Gen 19:15-30).