Deuteronomy 25:18

18 how he attacked you when you were tired, barely able to put one foot in front of another, mercilessly cut off your stragglers, and had no regard for God.

Deuteronomy 25:18 Meaning and Commentary

Deuteronomy 25:18

How he met thee by the way
Not with necessary provisions, food and drink, which would have been but a piece of kindness and humanity to travellers; but met them sword in hand, in order to stop their journey, and make them captives, at least to harass and distress them:

and smote the hindmost of thee;
came upon them in a sly cowardly manner, and attacked their rear:

[even] all [that were] feeble behind thee:
women and children, and such men as were weak, sickly, labouring under some disorder, and so lagged behind, and could not keep up with the rest; on these Amalek first fell, and began his attack here:

when thou [wast] faint and weary;
with travelling, and the more so for want of water, which was their case at Rephidim, when Amalek came out against them; which is another aggravation of their unkind usage of them they were not to forget:

and he feared not God;
who was then in the pillar of cloud and fire with Israel, which phenomenon Amalek might see, and yet did not fear; and who had done such wonders for Israel in Egypt, and had brought them from thence, and had drowned Pharaoh and his host in the Red sea, of which doubtless Amalek had heard, and yet feared not the Lord, who had done such great things.

Deuteronomy 25:18 In-Context

16 Dishonest weights and measures are an abomination to God, your God - all this corruption in business deals!
17 Don't forget what Amalek did to you on the road after you left Egypt,
18 how he attacked you when you were tired, barely able to put one foot in front of another, mercilessly cut off your stragglers, and had no regard for God.
19 When God, your God, gives you rest from all the enemies that surround you in the inheritance-land God, your God, is giving you to possess, you are to wipe the name of Amalek from off the Earth. Don't forget!
Published by permission. Originally published by NavPress in English as THE MESSAGE: The Bible in Contemporary Language copyright 2002 by Eugene Peterson. All rights reserved.