Matthew 23:33 You serpents, you generation of vipers,

KJV Verse: 

Mat 23:33 Ye serpents, ye generation of vipers, how can ye escape the damnation of hell?

Greek Verse: 

Literal Alternative: 

Snakes, offspring of treachery, how in the world might you get away from the choice of the trash heap.

Interesting and Hidden Aspects: 

The word translated as "serpent" means "snake," but it is also a kind of fish. The "serpent" was used by Christ both as a metaphor for wisdom (Mat.10:16) and, of course, an evil cunning.

The word translated as "generation" means "that which born or produced", "offspring," generally, any "product" or "work."

"Vipers" referred to all types of snakes, both poisonous and constrictors. It is a metaphor for treachery. Here the treachery referred to is the murder of the prophets.

"Generation of vipers" would probably be better translated as "offspring" or "the work" of "vipers" or "the treacherous." See Matt 12:34 for an earlier formulation of this same idea.

The word translated as "how" means "how in the world", "by any means," and "in any way." It is more expressive than a simple "how."

"Can you escape" is translated from a Greek word that means "to flee", "escape," and "to take flight." The word usually translated as "can" in English is not used here. However, the word is in a form indicating something that "might" happen. The tense is that of something happening at some point in time, which is usually translated as the past in English.

A word is untranslated here that means "from" in location and when referring to a source.

The Greek word translated as "damnation" means distinguishing among choices and "separating" things. Christ uses it in a variety of ways, though the KJV usually translates it as "judgment." It also means a "turning point," since it is the source of the meaning of "crisis" has in English. Only secondarily does it means "judgment" as in a court judgment.

"Hell" is from the Greek word for Gehenna, the valley of Hinnom (the Hebrew word), south of Jerusalem where trash, including diseased animals and human corpses was burned. A constant fire was kept burning there. This area was originally where children were sacrificed to Baal, and Baal (Beelzebub, "lord of the flies") is the name that Christ says others call him as the personification of evil. See this article on the words for "hell".  

Greek Vocabulary: 

ὄφεις (noun pl masc voc/nom/acc) "Serpents" is from ophis, which means "serpent", "a serpent-like bracelet", "a specific constellation", "a creeping plant," and "a type of fish." It is a metaphor for "an arrow."

γεννήματα (noun pl neut voc/nom/acc) "Generation" is from gennema, which means "that which born or produced," "offspring", "fruits" (of the earth), generally, any "product" or "work", "breeding", "begetting," and "producing."

ἐχιδνῶν, (noun pl fem gen) "Vipers" is echidna, which means "viper", "constrictor snake," and is a metaphor for a treacherous wife or friend.

πῶς "How" is from pos, which means "how", "how in the world", "how then", "in any way", "at all", "by any means", "in a certain way,"and "I suppose."

φύγητε (verb 2nd pl aor subj act) "Can ye escape" is pheugo, which means "to flee", "to take flight", "avoid", "escape", "seek to avoid", "to be expelled", "to be driven out", "go into exile", "go into banishment", "to be accused", "to be plead in defense," and "to flee from a charge." -

ἀπὸ Untranslated is apo, a preposition of separation which means "from" or "away from" from when referring to place or motion, "from" or "after" when referring to time, "from" as an origin or cause.

τῆς κρίσεως (noun sg fem gen) "Damnation" is from krisis, which means "separating", "distinguishing", "judgment", "choice", "election", "trial", "dispute", "event," and "issue."

τῆς γεέννης; (noun sg fem gen) "Hell" is geenna which is Greek for Gehenna, the valley of Hinnom (the Hebrew word), south of Jerusalem where trash, including diseased animals and human corpses was burned. Constant fires were kept burning there.

Wordplay: 

"Vipers" is a metaphor for treachery, connecting this with the previous verse. 

The words for "generation" (gennema) and "hell (geenna)  sound alike in Greek. 

The Spoken Version: 

"Snakes?" he suggested.

He held out one hand, indicating his accusers.

"The product of vipers?" he asked, holding out the other hand and balancing it against the first as if testing to see which fit best.

The crowd giggled. Christ looked at them and shrugged.

Then he looked again to his accusers, and put his hands on his hips, and asked sincerely, "How in the world can you possibly avoid your preference for the burning trash heap?"

The crowd laughed.

Related Verses: 

Jul 3 2016