Would Jesus have suggested to his followers
that they act in a sinful fashion?
Is stealing a sign (part of baseball) on par with rebellion against God’s law? Is “getting away with” scoring an illegal goal (part of soccer rules) because the referee did not see the action (part of human limitation in a sporting event) the basis for wrongdoing? I believe we need to make a theological assumption at this point: Jesus would not have told his disciples to sin (cf. James 1:13).
Matthew 10:16 is wrapped in a pericope whose direct instruction is for how to interact with a world which will reject The Message as well as the messengers. In fact, the context seems to suggest a violent response. The word in question is linked directly (“therefore”) to the preceding statement “I send you out as sheep among the wolves.” Rejection (10:14), deception (10:17), physical punishment (10:17), and illegal internment (10:18) before unjust authorities (10:19) is the lot of those who speak in The Name. Amid the command to be shrewd is the imperative “beware”—to watch out, be on one’s guard (Matt 7:15; 16:6, 11, 12; Luke 20:46; etc.). Jesus is saying believers are not to be naïve, unnecessarily provocative, unsuspecting, or ignorant of the schemes of those bent on our destruction (cf. Eph 6:11; 2 Cor 11:3). The idea of “cunning” resident within the instruction Jesus gives (10:11-20) is clearly an encouraged character trait.
Luke 16 is the parable of the unjust steward which has direct connection to Jesus’ commendation of “shrewdness” (16:8). While “dishonesty” is not lost upon the reader, the attitude behind the action is clearly approved. The steward sought those who would benefit from his “cutting a deal” securing acceptance by others after his firing. Our Lord suggests that people of the light should attract and keep close those who might come to faith (16:9) rather than driving them away, putting off people by, perhaps, a poor attitude. The unjust steward was providing for his own future—after his “pink slip” from the employer he had “greased the skids” in anticipation of his next position. Diplomacy is being used to accomplish one’s ends; in this case, a self-centered motive. Instead of attraction for future gain (heaven) Jesus seems to lament that believers instead drive away the very people who would be reached.
In both contexts, the idea of “cunning” seems to indicate planning ahead, foresight, using what is at one’s disposal to procure necessities for the future. Jesus acknowledges one aspect of the steward’s approach to his situation and in so doing suggests that believers use what earthly goods they have now for benefit of The Kingdom now and not yet (16:9). This same kind of wisdom is viewed by Jesus as preparedness (Matt 25:1-14) within the positive perspective of “faithfulness” (Matt 24:45). Surely the wise builder (Matt 7:24) planned ahead.
The adjacent metaphor of “serpent” seems to have its antecedent in subtlety as in Genesis three. A snake is symbolic of deception (notably Jesus calls the Pharisees as much in Matt 3:7; 12:34; 23:33) and cunning (2 Cor 11:3). Serpents lurk in unexpected places (Gen 49:17; Ecc 10:8; Am 5:19) while their ability to discern paths among the rocks is described as a mystery which cannot be understood (Prov 30:19). The wisdom literature itself seems to suggest the enigma of an eagle, virgin, ship, and snake is the ability of each to find its way without a guide, privy to no map, discovering the best way on its own.
Paul seems to have practiced a certain kind of canniness—his own personal “getaway” —in dealing with pagans. Reading Acts 21:27-26:32 one retains the distinct impression that Paul was nimble with his words, adroit in employment of his citizenship, and schooled in using societal law for his own ends. Acts 24:16 marks the purity of motive while using “the system” for Paul’s own ends: clearly a shrewd move. Paul’s ministry began with intrigue. He used clandestine information and a cunning escape to combat his enemies (Acts 9:23-25). “Try to be kind to everyone” (1 Thess 5:15) is as interesting a phrase as “if it is possible, as far as it depends on you, live at peace with all men” (Rom 12:18). Obviously, while we should not look for trouble we should be ready for it.
Furthermore, the apostle commands “be careful how you live, not as unwise but as wise” (Eph 5:15). In communication with “outsiders” Christians are told to be “wise” seasoning speech with “salt” (Col 4:5-6). Perhaps Titus 2:1-10 best expresses the sentiment of how Christians are to present themselves to the culture. The three purpose clauses (“so that” 2:5, 8, 10) demand believers live life in a proper attitude with attraction as the end result.
Based on the context of Matthew 10 and corollary passages I might suggest a definition of “shrewdness” as preparing for the future, ever mindful of potential enemy tactics, savvy in dealings with unbelievers. Christians should be serpent-like in their exercise of caution and wariness. Instead of a “frontal assault,” a feint “up the middle” while “circling ‘round the flank’” might be a better tactic living in a pagan world. As soldiers say, discretion is the better part of valor. Clear motives are in evidence as is the astute ability to stay out of harm’s way. Diplomacy without compromise is a biblical moniker. We must find a way to move forward, speaking truth in love, much as did William Wilberforce in eliminating the English slave trade. We play by the rules of corrupt systems for the benefit of The Kingdom so that no one will have anything bad to say about us. We do not revel in “missed calls” as an excuse for unethical performance but make good use of all allowable plays to “score.” Shrewdness is an attitude of understanding to know how corrupt culture works while clearly living life within transcendent ethical boundaries.
Mark is definitely in favor of “the play action pass” a wonderful form of deception in football. This article was originally written in July, 2008.
 The vicious imagery is resident within both testaments (Ezek 22:27; Zeph 3:3; Acts 20:29). It is important to comprehend that even though Jesus is forcefully sending his disciples (literally, “I myself am sending”) He is their Shepherd (John 10:11, 14, 27, 28; cf. 1 Peter 5:1-4) unlike those who are in danger without a guardian (cf. Matt 9:36).