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

Spoken to
audience

A long condemnation of the religious leaders of the time,

KJV

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

NIV

Matthew 23:33 “You snakes! You brood of vipers! How will you escape being condemned to hell?

LISTENERS HEARD

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

MY TAKE

There are snakes, and there are the offspring of snakes.

LOST IN TRANSLATION

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

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

# KJV TRANSLATION ISSUES
5
  • WW - Wrong Word -- The word translated as "can" should be something more like "should."
  • CW - Confusing Word -- The "escape" does not capture the specific meaning of the word.
  • WW - Wrong Word -- The word translated as "damnation" should be something more like "judgment."
  • MW - Missing Word -- The word "the" before "hell" is not shown in the English translation.
  • CW - Confusing Word -- The "hell" does not capture the specific meaning of the word.
# NIV TRANSLATION ISSUES
7
  • WW - Wrong Word -- The word translated as "will" should be something more like "should."
  • CW - Confusing Word -- The "escape" does not capture the specific meaning of the word.
  • IW - Inserted Word -- The word "being" doesn't exist in the source.
  • WW - Wrong Word -- The word translated as "condemned" should be something more like "judgment."
  • WF - Wrong Form -  The "condemned" is not an active verb but a noun, "judgment."
  • MW - Missing Word -- The word "the" before "hell" is not shown in the English translation.
  • WW - Wrong Word -- The word translated as "to" should be something more like "of."
  • CW - Confusing Word -- The "hell" does not capture the specific meaning of the word.
EACH WORD of KJV

Ye - This is from the vocative form of the noun that means it names the person being talked to.

serpents, -- The word translated as "serpent" means "serpent" and "snake". The "serpent" was used by Jesus both as a metaphor for wisdom (Mat.10:16) and, of course, evil cunning. This is a reference to the Hebrew in Genesis 3:1, where the serpent is described as the cleverest of all animals. The bronze or brass snake raised by Moses in the desert to cure the Israelites of snakebite is a symbol for Christ being raised on

ye - This is from the vocative form of the noun that means it names the person being talked to.

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

of -- This word "of"  comes from the genitive case of the following word that requires the addition of a preposition in English.  The most common is the "of" of possession.

vipers,  - "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.

how  - 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 -- (WW) This helping verb "can" does not indicate abillity, but that the verb describes a possibility, the subjunctive voice. A "might" or "should" in English is more appropriate, but is assumed in an "if/when/whoever/except" clause. Helping verbs are not needed in Greek since the main verb carries this information in its form.

ye - This is from the second-person, plural form of the verb.

escape  - (CW) "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.

the - The word translated as "the" is the Greek definite article, without a noun, it has the sense of "the one." The Greek article is much closer to our demonstrative pronouns ("this," "that," "these," "those") than the English "the." See this article for more. 

damnation  -  (WW) 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.

of -- This word "of"  comes from the genitive case of the following word that requires the addition of a preposition in English.  The most common is the "of" of possession.

missing "the"  -- (MW) The untranslated word is the Greek definite article, which usually precedes a noun and, without a noun, takes the meaning of "the one." The Greek article is much closer to our demonstrative pronouns ("this," "that," "these," "those"). See this article for more. 

hell?  - (CW) "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.
 

EACH WORD of NIV

You - This is from the vocative form of the noun that means it names the person being talked to.

snakes, -- The word translated as "snakes" is also a kind of fish. The "serpent" was used by Jesus both as a metaphor for wisdom (Mat.10:16) and, of course, evil cunning. This is a reference to the Hebrew in Genesis 3:1, where the serpent is described as the cleverest of all animals. The bronze or brass snake raised by Moses in the desert to cure the Israelites of snakebite is a symbol for Christ being raised on

you - This is from the vocative form of the noun that means it names the person being talked to.

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

of -- This word "of"  comes from the genitive case of the following word that requires the addition of a preposition in English.  The most common is the "of" of possession.

vipers,  - "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.

How - 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."

will -- (WW) This helping verb "will" does not indicate the future tense, but that the verb describes a possibility, the subjunctive voice. A "might" or "should" in English is more appropriate, but is assumed in an "if/when/whoever/except" clause. Helping verbs are not needed in Greek since the main verb carries this information in its form.

you - This is from the second-person, plural form of the verb.

escape  - (CW) "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.

being -- (IW) There is nothing that can be translated as "being" in the Greek source.

missing "the"  -- (MW) The untranslated word is the Greek definite article, which usually precedes a noun and, without a noun, takes the meaning of "the one." The Greek article is much closer to our demonstrative pronouns ("this," "that," "these," "those"). See this article for more. 

condemned -  (WW, WF) The Greek word translated as "condemned " 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.

to -- (WW) This word "to"  comes from the genitive case of the following word that requires the addition of a preposition in English.  The most common is the "of" of possession. However, it can also mean "belonging to," "part of," "which is," "than" (in comparisons), or  "for," "concerning" or "about" with transitive verbs.

missing "the"  -- (MW) The untranslated word is the Greek definite article, which usually precedes a noun and, without a noun, takes the meaning of "the one." The Greek article is much closer to our demonstrative pronouns ("this," "that," "these," "those"). See this article for more. 

hell?  - (CW) "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.

COMPARISON: GREEK to KJV

ὄφεις [7 verses](noun pl masc voc/nom/acc) "Serpents" is 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 [5 verses](noun pl neut voc/nom/acc) "Generation" is gennema, which means "that which born or produced," "offspring," "fruits" (of the earth), generally, any "product" or "work," "breeding," "begetting," and "producing."

ἐχιδνῶν, [2 verses](noun pl fem gen) "Vipers" is echidna, which means "viper," "constrictor snake," and is a metaphor for a treacherous wife or friend.

πῶς [36 verses](pron indecl form) "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 [7 verses](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 [190 verses]​(prep) 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 [821 verses](article sg neut dat)  "The" is the Greek definite article, hos, ("the"). 

κρίσεως [26 verses](noun sg fem gen) "Damnation" is krisis, which means "separating," "distinguishing," "judgment," "choice," "election," "trial," "dispute," "event," and "issue."

τῆς [821 verses](article sg fem gen))  Untranslated is the Greek definite article, hos, ("the"). 

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. 

Unimportant Opinions and Imaginings

"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.

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