Now the serpent was more crafty than any of the wild animals the LORD God had made. He said to the woman, "Did God really say, 'You must not eat from any tree in the garden'?" - Genesis 3:1

15I will most gladly spend and be expended for your souls. If I love you more, am I to be loved less? 16But be that as it may, I did not burden you myself; nevertheless, crafty fellow that I am, I took you in by deceit. 17Certainly I have not taken advantage of you through any of those whom I have sent to you, have I?… 2 Corinthians 12: 15-17

These two verses have something in common. They both use "crafty" to describe the character of something or someone. In Genesis it is the writer of Genesis who describes the serpent as "crafty" in 2 Corinthians 2:15-17 it is the apostle Paul himself who describes himself as "crafty". Paul explains that he did not take advantage of anyone through his disciples but he himself was crafty and deceitful.... Why would Paul even used these words to describe his actions.  

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Now the serpent was more crafty than any beast of the field which the Lord God had made…Genesis 3:1

The Hebrew word translated “crafty” is aruwm (עָרוּם ). The word has positive and negative meanings, as evidenced by its alternate translations in our English bibles. For example:

A prudent (aruwm) man conceals knowledge, But the heart of fools proclaims folly. Proverbs 12:23

Paul used a Greek word, panourgos πανοῦργος :

But be that as it may, I did not burden you myself; nevertheless, crafty (panourgos) fellow that I am, I took you in by deceit. 2 Corinthians 12:16

That word only appears once in the New Testament, but if you are right that it is comparable to the Hebrew aruwm, then panourgos must have a positive meaning (“prudent”) like it has a negative one (“crafty”). I wonder why the translators chose the negative word rather than the positive one?

Thanks for your reply: Indepth study requires collaboration. The problem I face is most "Christians" don't value critical thinking as a must.  When used in 2 Corinthians 12:16 -
King James Bible
But be it so, I did not burden you: nevertheless, being crafty, I caught you with guile.  In the NIV it reads - Be that as it may, I have not been a burden to you. Yet, crafty fellow that I am, I caught you by trickery!  The KJV uses "guile" and the NIV "trickery" or "deceit" as other translations might render neither of which is positive. The first time "crafty" is used in Genesis 3:1 it is used negatively to describe the character of Satan. Paul uses it  to describe himself or his actions.  So, the question for me is; if this is a bad translation of "crafty" which can be used in a positive sense, how does one explain the last portion of the sentence that says Paul caught, or took them by "trickery"? Can trickery have a positive aspect as well?

Fascinating discussion, chaplain.

The Greek word translated "guile" in the KJV and "trickery" in the NIV is dolos (δόλος). From its usage in the New Testament, it does appear to be wholly negative in meaning. The use Paul makes of it In 1 Thessalonians 2:3 is typical: 

For our exhortation was not of deceit, nor of uncleanness, nor in guile (dolos).

Why Paul would avoid guile when dealing with the Thessalonians and embrace guile when dealing with the Corinthians, I cannot fathom. 

As I read the 2 Corinthians passage over and over, I genuinely wonder whether Paul is intending a confession of trickery. In verse 14 he claims not to have been financially burdensome for the church, in verse 15 he says he's willing "to be spent" for their sakes, in verse 17 he asks rhetorically whether he or his emissaries ever took advantage of the saints. In its entirety, the passage seems designed to help the apostle defend himself. So I have to wonder, is Paul being sarcastic in verse 16? Is he mordantly repeating an accusation made of him that he is "crafty" and uses "guile"? That may be the assumption of the Amplified Bible's paraphrase of the verse:

But though granting that I did not burden you [with my support, some say that] I was crafty [and that] I cheated and got the better of you with my trickery.

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