וְרָדְפ֨וּ מִכֶּ֤ם חֲמִשָּׁה֙ מֵאָ֔ה וּמֵאָ֥ה מִכֶּ֖ם רְבָבָ֣ה יִרְדֹּ֑פוּ וְנָפְל֧וּ אֹיְבֵיכֶ֛ם לִפְנֵיכֶ֖ם לֶחָֽרֶב׃
Cinq d’entre vous en poursuivront une centaine, et cent d’entre vous une myriade; et vos ennemis tomberont devant votre glaive.
Tze'enah Ure'enah
“Five of you shall give chase to a hundred and a hundred of shall give chase to ten thousand” [26:8]. Five Israelites will pursue a hundred gentiles and a hundred will pursue ten thousand. Here one asks a question, why will one hundred pursue ten thousand, when five will only pursue one hundred gentiles. The calculation is that one hundred Israelites should pursue two thousand gentiles. The explanation is that it is not the same when many Israelites are together. Their merit is much greater than when a few are together. That is to say, the Holy One hears the prayers of many people more quickly than that of a few people. Even if the five are more pious than a hundred men, yet it is better when many Israelites are together. Therefore, each one of the hundred kills more than the number that are killed by the five men.3Rashi, Leviticus, 26:8.
Rashi
ורדפו מכם [AND FIVE] OF YOU SHALL PURSUE [A HUNDRED] — five of the weakest among you — and not alone of the most robust among you (Sifra, Bechukotai, Chapter 2 4).
Ramban
AND YOUR ENEMIES SHALL FALL BEFORE YOU BY THE SWORD. He assured them at first that they would chase their enemies and that they would fall by their sword,25See Verse 7. and then He stated again by way of repetition [in the verse before us], and your enemies shall fall before you by the sword, in order to give them fortitude of heart and strength so that five [of them would not be afraid] to pursue a hundred. He [furthermore promised that He] would put faintness into the heart of their enemies, so that a hundred would [in fact] flee before five, and would all fall by the sword of the five, for it would be possible that they [a hundred people] would flee because of the sword and because of their fear, but that they would not be able to kill them by the sword because of their few numbers [therefore He mentioned specifically that they would be able to put them to the sword too]. Rabbi Abraham ibn Ezra has said that this repetition [in our verse] means that they [the enemies] will fall continually, time after time, without regaining [their strength].
Rabbeinu Bahya
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חמישה מאה ומאה מכם רבבה FIVE [OF YOU SHALL PURSUE] A HUNDRED AND A HUNDRED… TEN THOUSAND — But is this the right proportion? Surely it should have stated only “and a hundred of you shall pursue two thousand (and not ten thousand)!? But the explanation is: a few who fulfill the commandments of the Torah cannot compare with the many who fulfill the commandments of the Torah (i. e. the greater the group of those loyal to the Torah, the greater is the morale and, under God’s blessing, the physical strength of each individual belonging to the group) (Sifra, Bechukotai, Chapter 2 4).