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Habakkuk 2:16 English Standard Version

You will have your fill of shame instead of glory. Drink, yourself, and show your uncircumcision! The cup in the LORD’s right hand will come around to you, and utter shame will come upon your glory!

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This section of Hab 2 contains four woes against the Chaldeans:

  1. V6 - Woe to him who amasses what is not his and makes himself rich with many loans! ...
  2. V9 - Woe to him who builds his house by unjust gain, ...
  3. V12 - Woe to him who builds a city with bloodshed and establishes a town by iniquity! ...
  4. V15 - Woe to him who gives drink to his neighbors, pouring it from the wineskin until they are drunk, in order to gaze at their nakedness!

V16 is variously translated - the BSB gives a good rendering:

You will be filled with shame instead of glory. You too must drink and expose your uncircumcision! The cup in the LORD’s right hand will come around to you, and utter disgrace will cover your glory.

The verb translated "expose your uncircumcision" is וְהֵֽעָרֵ֑ל (wə·hê·‘ā·rêl) and is used in an extremely pejorative way. Note the meaning of BDB here -

Niph`al Imperative הֵעָרֵל Habakkuk 2:16 be counted uncircumcised, i.e. be object of mockery;

Strong's is also helpful with the meaning of this word-

A primitive root; properly, to strip; but used as denominative from arel; to expose or remove the prepuce, whether literal (to go naked) or figurative (to refrain from using) -- count uncircumcised, foreskin to be uncovered.

Thus, Habakkuk is pronouncing a woe of extreme mockery about what shame the Chaldeans heap upon themselves when they get drunk. Note the great emphasis of shame and disgrace suffuses the surrounding text and also the repetition of "skin" as "wineskin" and "foreskin" [= nakedness] -

15 Woe to him who gives drink to his neighbors, pouring it from the wineskin until they are drunk, in order to gaze at their nakedness!

16 You will be filled with shame instead of glory. You too must drink and expose your uncircumcision! [foreskin = nakedness/shame] The cup in the LORD’s right hand will come around to you, and utter disgrace will cover your glory.

The Pulpit commentary suggests:

Verse 16. - Just retribution falls on Babylon. Thou art filled with shame for glory. Thou art satiated, indeed, but With shame, not with glory. Thou hast revelled in thy shameless conduct to the defencelses, but this redounds to thy dishonour, and will only add to the disgrace of thy fall The Septuagint joins this clause with part of the following: "Drink thou also fulness of shame for glory." Drink thou also the cup of wrath and retribution. Let thy foreskin be uncovered. Be thou in turn treated with the same ignominy with which thou hast treated others, the figure in ver. 15 being here repeated (comp. Lamentations 4:21). It is otherwise translated, "Be thou," or "show thyself, uncircumcised." This, in a Jew's eyes, would be the very climax of degradation.

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