Tl;dr Jacob was the chosen one, but in many instances, he lacked faith in God. Instead, he often relied on his own wit to achieve his ends.
“Sell now your birthright to me.”(25:31) Certainly, something as sacred as the birthright is not meant to be part of a business transaction. Instead, God, given his covenant with Abraham, should be the one who blesses Jacob the responsibility of inheritance. The birthright is sacred because of the “everlasting” covenant God made with Abraham that will continue through Abraham’s “seed”. In other words, whoever (Jacob or Esau) has the birthright will automatically inherit the covenant with God. This covenant includes God’s promise that the recipient would be the “father to a multitude of nations” and owner of “the whole land of Canaan” (17:5-10). Hence, the responsibility of inheritance is a heavy and sacred one.
However, Esau proves to be undeserving of this birthright as he values it less than a bowl of stew. On the other hand, Jacob is less of a barbarian than Esau, and is a tent-dweller like Abraham. Therefore, it seems that Jacob is more deserving of the birthright than Esau. Indeed, Jacob’s superiority is divinely ordained even before birth; “people over people shall prevail, the elder, the younger’s slave”. So if Jacob was meant to be the chosen one, why did he use deceit to gain the birthright? After all, if Jacob believed in the divine will of God, he would have trusted God to give the birthright to the more deserving son. Thus, when Jacob’s acted to secure the birthright, it showed his lack of faith in God’s ability to ensure that the birthright is passed on to the most worthy son.
Additionally, Jacob bargains with God at the end of chapter 28. Jacob says “IF the LORD God be with me and guard me… then the LORD will be my God.” This clearly illustrates Jacob’s doubt over whether God would keep his promise. In comparison, Abraham did not even bargain when he was ordered by God to sacrifice his beloved son. This contrast highlights Jacob’s lack of faith in God.
Moreover, there are numerous instances in which Jacob relied on his wit to achieve his goals. But is there a need for deceit and cunning? If Jacob has the blessings of God, wouldn’t things eventually end up in Jacob’s favour? Therefore, Jacob’s use of strategy and wit (e.g. the use of selective breeding to grow his own flock, pacifying Esau by sending tributes, splitting his family into two) illustrates his fears, such as his fear for the loss of life and fortune. The fact that God’s covenant with him did not assuage these fears shows again that Jacob lacks faith in God.
Last but not least, Jacob’s night wrestle with the mysterious creature can conceivably be seen as Jacob’s struggles with his faith. The long wrestle from night to dawn may be symbolic of Jacob’s equally arduous struggle with his faith since young. However, the episode ends with Jacob calling out “I have seen God face to face and I came out alive” (32:32). The renaming of Jacob as Israel is also significant a turning point. Perhaps it is a sign of Jacob’s renewed faith in God.