Astuteness or craftiness in dealings with others, especially in using one’s understanding and judgment to one’s own advantage. Scripture commends it when it is seen in wise words and actions directed towards a worthy goal, but condemns it when it takes the form of cunning and deceitful scheming for sinful and selfish ends.
Shrewdness as astuteness
Jesus Christ’s wisdom in answering his enemies Mt 22:18-22 pp Mk 12:15-17 pp Lk 20:23-26 on the matter of paying taxes to Caesar; Mt 22:31-32 pp Mk 12:26-27 pp Lk 20:37-38 on the question of the resurrection; Jn 8:7 regarding the woman caught in adultery
Further examples of astuteness 1Sa 23:22-23 David’s shrewdness in fleeing from Saul; 2Sa 14:1-3 Joab’s ruse to persuade David to call Absalom back from exile; 1Ki 3:28 Solomon’s wise judgment; 2Ch 11:23 Rehoboam acts wisely to secure his kingdom; Da 1:11-13 Daniel avoids eating royal food and wine; Mt 2:16 Herod is outwitted by the Magi; Mk 7:27-29 pp Mt 15:26-28 the Syro-Phoenician woman’s wise response
Shrewdness as crafty and deceitful scheming
It is condemned by God 2Sa 22:26-27 pp Ps 18:25-26 God is shrewd in dealing with those who cleverly deceive others; Job 5:12-13 See also Ps 94:11; Pr 6:12-15; Pr 12:2; Isa 5:21; Isa 44:24-25; 1Co 1:19; Isa 29:14; 1Co 3:19-20
The craftiness of Jesus Christ’s enemies Mt 22:15-17 pp Mk 12:13-15 pp Lk 20:20-22 The Pharisees try to trap Jesus Christ over paying taxes; Mt 26:3-4 pp Mk 14:1-2 pp Lk 22:1-2 The religious leaders plot Jesus Christ’s death.
Further examples of crafty scheming Ge 25:31-33 Jacob buys Esau’s birthright; Ge 27:15-16 Isaac is tricked into blessing Jacob; Ex 1:10 Pharaoh plans to reduce the number of Israelites; Jos 9:3-6 The Gibeonites deceive Joshua; 2Sa 13:3 Jonadab plots for Amnon against Tamar; Ne 6:2-13 schemes against Nehemiah; 2Co 12:16 Paul sarcastically echoes the slander against him that he tricked people into giving him money.