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The Bible has many metaphors for many things. Some of them use the same item in two different contexts in two different ways. Immediately, I can think of Christ's use of the word "sign" and how he would and would not provide one (John has seven signs which demonstrate Christ as Lord, but the Synoptics say that signs will not be given). The asp was something deadly and was a sign of wickedness, but when it was raised on a staff, it became a instrument of healing.
I think that "serpent" here is probably just a snake.
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I think its a great metaphor.. we should be as wise as the enemy because if you are not as wise as he is then how can you protect yourself from his attacks? Not being conniving like him but wise as him.. Just because we are to be as wise as he is does not mean we do as he does. That's where the harmless part comes in. Example, if you have a group of people you hang with.. Your discernment will show you the ones who mean you no good and even though you are wise enough to recognize their evil intentions for you, doesn't mean you react negatively to them. Wise as them but humble! Hope that makes any sense!
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Devil-serpent-satan. Bible refers to satan as serpent not serpents
Rev 20 vrs 2 (NIV). He se seized the dragon that ancient serpent, who is the devil, or Satan, and bound him for thousand years.
Snake-snakes- serpents. Mat 10 vrs 16 (NIV). I am sending you out like sheep among wolvesn. Therefore be shrewd as snakes and as innocent as doves.
Mat 10 vrs 16 (KJV). Behold, I send you forth as sheep in the midst of wolves, be ye therefore wise as serpents, and harmless as doves.
Even whithout reference, how can a single Satan be serpents.