to ascend · verb, qal perfect, 3rd person masculine singular
city
עִ֣יר'ir
H5892
a city (a place guarded by waking or a watch) in the wi… · noun, common feminine singular construct
mighty
גִּ֭בֹּרִיםGi.bo.rim
H1368
powerful · noun, common masculine plural absolute
down
וַ֝יֹּ֗רֶדvai.Yo.red
H3381
to descend (literally · conjunction + verb, hiphil sequential imperfect, 3rd person masculine singular
strength
עֹ֣ז'oz
H5797
strength in various applications (force · noun, common masculine singular construct
confidence
מִבְטֶחָֽהmiv.te.Chah
H4009
properly · noun, common masculine singular construct + pronominal suffix, 3rd person feminine singular
Strong's Exhaustive Concordance (James Strong, 1890/1894), public domain; digitized by Open Scriptures (CC BY-SA). KJV word tagging: eBible.org (public domain). Original-language text, parsing and brief lexicon: STEPBible.org data from Tyndale House, Cambridge (CC BY 4.0).
Cross-references
Ecclesiastes 7:19 Wisdom strengtheneth the wise more than ten mighty men which are in the city.
Proverbs 24:5 A wise man is strong; yea, a man of knowledge increaseth strength.
Ecclesiastes 9:13-18 This wisdom have I seen also under the sun, and it seemed great unto me:
2 Samuel 5:6-9 And the king and his men went to Jerusalem unto the Jebusites, the inhabitants of the land: which spake unto David, saying, Except thou take…
2 Samuel 20:16-22 Then cried a wise woman out of the city, Hear, hear; say, I pray you, unto Joab, Come near hither, that I may speak with thee.
Cross-references from OpenBible.info (CC BY), in the lineage of the Treasury of Scripture Knowledge (public domain).
Commentary
Matthew Henry on Proverbs 21:22
Note, 1. Those that have power are apt to promise themselves great things from their power. The city of the mighty thinks itself impregnable, and therefore its strength is the confidence thereof, what it boasts of and trust in, bidding defiance to danger. 2. Those that have wisdom, though they are so modest as not to promise much, often perform great things, even against those that are so confident of their strength, by their wisdom. Good conduct will go far even against great force; and a stratagem, well managed, may effectually scale the city of the mighty and cast down the strength it had such a confidence in. A wise man will gain upon the affections of people and conquer them by strength…
"Wisdom is better than strength" (Ecc 7:19; Ecc 9:15).
strength . . . thereof--that in which they confide.
John Gill on Proverbs 21:22
A wise man scaleth the city of the mighty,.... Which makes good what is elsewhere said, that "wisdom is better than strength", Ecclesiastes 9:16; and sometimes more is done by prudence and wisdom, by art and cunning, by schemes and stratagems, than by power and force; especially in military affairs, and particularly in besieging and taking fortified cities; when one wise man, by his wisdom, may so order and manage things, as to be able, with a few under his command, to mount the walls of a city and take it, though defended by a mighty garrison in it. This may be applied to, our Lord Jesus Christ entering into the city of a man's heart, possessed by the strong man armed; overcoming him, takin…
22 A wise man scaleth a city of the mighty;
And casteth down the fortress in which they trusted.
Ecc 9:14. is a side-piece to this, according to which a single wise man, although poor, may become the deliverer of a city besieged by a great army, and destitute of the means of defence. עלה, seq. acc., means to climb up, Joe 2:7; here, of the scaling of a fortified town, viz., its fortress. עז is that which makes it עיר עז, Isa 26:1 : its armour of protection, which is designated by the genit. מבטחה, as the object and ground of their confidence. The vocalization מבטחה, for mibtachcha (cf. Jer 48:13 with Job 18:14), follows the rule Gesen. 27, Anm. 2b. The suff., as in לאתננּה, Isa 23:17, is lig…
The Church Fathers
"The wise man occupied fortified cities and destroyed the stronghold in which the impious trusted." Do you suppose that, when Solomon said these things, he wished to teach us this — that "the wise man captured cities and destroyed strongholds" built of stones? Or does it rather indicate that the city and the walls are the dogmas of the impious and the syllogisms of the philosophers, by which they construct all manner of impious things contrary to the divine law, which are observed among the pagans or the barbarians? But those things too must be reckoned among these, and to be "fortified cities" and set upon mountains, which the heretics place in their assertions from the Scriptures as though upon high mountains. These "cities," then, every "wise man" who preaches the word of truth "has destroyed," and he has overthrown the cities of falsehood with the battering-ram of truth, just as the Apostle Paul also said: "destroying reasonings and every height that exalts itself against the knowledge of God."
The wise man ascends the city of the mighty, etc. The city of the mighty, he calls the world, which once, subjected to the tyranny of evil spirits, foolishly served, having confidence in the worship of those who are not gods, but the works of human hands (Psalm 115). This city was entered by the one born in the flesh, who is the power of God, and the wisdom of God (1 Corinthians 1:24). He destroyed through his preachers the worship of the gods, in whom they had trusted, ignorant of the truth, and taught that confidence should be placed in heavenly things, which could never be destroyed. But every day the wise man ascends the city of the mighty, and destroys the strength of its confidence, when any faithful teacher refutes the arguments of philosophers or heretics, or even the obstinate contradictions of carnal brothers, by which they strive to defend and alleviate their crimes, by the assertion of faith and the discipline of ecclesiastical correction, and, laying bare, annuls them.
The Church Fathers: public-domain translations (Ante-Nicene and Nicene and Post-Nicene Fathers), verse-indexed by SermonIndex (CC BY 4.0).
A wise military strategist can devise ways to defeat stronger forces. This makes wisdom superior to raw power (cp. Eccl 7:12; 9:13-18).
Rashi on Proverbs 21:22
A wise man ascended to a city of mighty men This refers to Moses, our teacher, who went up among the angels, who are mighty in strength. (and brought down, etc. The Torah.)