Be wise as serpents

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TonyChanYT

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Jesus gave a pep talk in Matthew 10:

16 Behold, I am sending you out as sheep in the midst of wolves, so be wise as serpents and innocent as doves. 17a Be on your guard.
What was so wise about serpents? What was this positive imagery about snakes?

Barnes explained:

sheep in the midst of wolves - That is, I send you, inoffensive and harmless, into a cold, unfriendly, and cruel world. Your innocence will not be a protection.
How do snakes survive in this cruel world?

Not by being innocent.

Be wise as serpents ... - Serpents have always been an emblem of wisdom and cunning, Genesis 3:1. The Egyptians used the serpent in their hieroglyphics as a symbol of wisdom. Probably the thing in which Christ directed his followers to imitate the serpent was in its caution in avoiding danger.
Be cautious, like a snake. Don't innocently head into trouble situations.

No animal equals them in the rapidity and skill which they evince in escaping danger. So said Christ to his disciples, You need caution and wisdom in the midst of a world that will seek your lives. He directs them, also, to be harmless, not to provoke danger, not to do injury, and thus make their fellow-men justly enraged against them. Doves are, and always have been, a striking emblem of innocence. Most people would foolishly destroy a serpent, be it ever so harmless, yet few are so hard-hearted as to kill a dove.
Jesus used snakes as positive imagery. Don't be foolish. Don't go out there looking for trouble. Be wise. Be cautious, like a snake.
 

Wick Stick

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Snakes mostly had a positive image in the Ancient Near East. In addition to being icons of wisdom (as you mentioned), they were also emblems of healing and resurrection, due to their habit of shedding their skin and looking brand-new. Even Moses raised up a brazen serpent as part of a healing miracle.

The Caduceus and Asclepius remain symbols of medicine to this day:

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