The theme of this saying is the power of wisdom to overcome (superior) physical strength. The picture is of a military campaign, which some commentators suggest reflects a real or fictional story that is now otherwise lost to us. There is close parallelism between the two lines of the verse.
“A wise man scales the city of the mighty”: “A wise man”, or as New Revised Standard Version and Contemporary English Version have it, “one wise person,” refers in this context to the commander of an army; hence Good News Translation “A shrewd general can take a city. . ..” “Scales” is a picture of soldiers attacking a city by “going up on” or “climbing over” its walls; the commander does not do this alone! Some versions render this as “attacks” (New International Version) or “can attack” (Revised English Bible); however, the point of the saying is that the wise commander succeeds in what he does, so renderings like “can defeat” (Contemporary English Version) or “can take” (Good News Translation) are more appropriate. Most translations render the verb as saying what the wise person is able to do; New Revised Standard Version, however, says “One wise person went up against. . .,” which makes the saying refer to a story that the original readers knew. “The city of the mighty” means a city defended by a strong force or by strong soldiers (“a city of warriors” New Revised Standard Version).
“And brings down the stronghold in which they trust”: “Brings down” is a causative verb that is quite general in its meaning. It does not indicate how the commander and his soldiers get the defenses of the city down. “The stronghold” or “fortress” (Contemporary English Version) is a rendering of the Hebrew noun “strength.” “In which they trust” has the sense of “that they relied on [to protect them].” The whole expression is most likely a reference to the strong walls of the city; hence Good News Translation “the walls they relied on” and New Jerusalem Bible “the rampart on which it relied.” If we accept this understanding, we should render the verb “brings down” in a way that is appropriate for the walls of a city; for example, “destroy” (Good News Translation), “shatter” (New Jerusalem Bible), or “break down.” In the warfare of much of the Old Testament period, machines such as battering rams were commonly used to break through the walls of a city, as an alternative to capturing it by going over the walls.
Quoted with permission from Reyburn, William D. and Fry, Euan McG. A Handbook on Proverbs. (UBS Helps for Translators). New York: UBS, 2000. For this and other handbooks for translators see here .

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