The story of Esav and Yaakov is a story of dueling models of manhood.
From the beginning, it is clear that of the twins, Esav is portrayed, as measured against a biblical and Ancient Near Eastern yardstick, as more “manly” than Yaakov. He is hairy, red or ruddy, and a hunter; all three are associated with masculine virility elsewhere in Tanakh and throughout the ANE and countless other cultures. He also gets married far earlier than his brother, which suggests sexual maturity.
Esav hunts tzayid, a term which appears overwhelmingly in Sefer Bereishit, and then only in reference to Esav and Nimrod. Nimrod is twice described as a gibbor tzayid; the word gibbor derived from the same root as gever, a man. In introducing the brothers, the Torah explicitly calls Esav a man twice, Yaakov only once. (ויהי עשו איש ידע ציד איש שדה ויעקב איש תם ישב אהלים.)
Yaakov, by contrast, is not a hunter but a shepherd (see Rashbam, Bechor Shor, and Ibn Ezra to איש תם). He tried to become the firstborn at birth but failed, exposing him as a follower, not a leader.
Yaakov was a cook, typically associated with femininity, and we find him in feminine spaces (with Rivkah), while his brother is out on the hunt (biblical scholars see hegemonic masculinity, or the ideal of manhood in a particular culture, as a man who spends the bulk of his time outside of feminine spaces).
In the cutthroat tribal world that was the Land of Canaan, particularly in the Negev where agriculture was scarce and famines were not uncommon (see the very next chapter) and especially because at the beginning of the story it appears that Yitzchak was not yet wealthy and relied on hunting for his next meal (כי ציד בפיו), Yitzchak understood the necessity of virile masculinity for survival in the new land his father had settled in.
Beyond answering a request for children, Yitzchak also experienced none of the miracles his father had experienced. The last he had seen of divine intervention involved a communication to his father at the Akeidah. During famine, while Avraham receives divine intervention to save him from Paroh and Avimelekh respectively, there will be no miracle to intervene and save Yitzchak. Rivkah received a prophecy, not Yitzchak. Rivkah only disagrees because she knows the angel’s prophecy, but not on principle. Yitzchak well understood the importance of strength and courage for survival.
Where, then, did Esav go wrong? Being a hunter was not intrinsically bad; Nimrod his predecessor was a “gibbor tzayid lifnei Hashem,” and there is ample reason to think that according to peshat Nimrod was righteous (see Ibn Ezra and Radak to Bereishit 10:9).
Esav went wrong because it quickly became clear that he lacked the self-discipline to cool his passions when he was off the battlefield, and sublimate his bloodlust to nobler or at least less harmful ends.
Esav was famished after the hunt, so he demanded food instead of requesting it. He cannot even recall the name of the lentil; instead he calls it האדום האדום הזה; his language is as course after the hunt as his behavior is while on the hunt - and his language reflects his essential character (על כן קרא שמו עשו). He uses only the short-term, desperate survival logic of the hunter-gatherer in foregoing long-term benefits (the firstborn) in favor of immediate gratification (soup). He was all action, no reflection (ויאכל וישת ויקם וילך).
Crucially and closely related, he also lacked the emotional self-awareness to recognize that his hatred for the firstborn was mere rationalization. As is boys’ nature, he desperately craved his fathers’ love, and so he did the one thing he knew would earn him his father’s love - hunt prey - but Esav was so focused on satisfying his father’s needs that he lost his inner forest for the trees.
Yaakov, meanwhile, is no hunter, but he is reliable, savvy, and able to set aside his passions for long-term gains - such as earning the firstborn and raising a committed family. Esav marries Hittite women, apparently without consulting his parents ahead of time, likely sowing doubts in his father’s mind about his worthiness to receive the beracha. And Yaakov is again able to outsmart his brother - and, importantly, to provide food - by substituting brains for brawn, scrupulousness for recklessness.
No wonder that by the time he realized Yaakov had outwitted both his father and brother, Yitzchak trembled in recognition that the judicious man was better suited to the blessing than the hunter of unbridled passion (see Radak, Malbim). Indeed, Yaakov, in the end, emerges as the better “man” (הן גביר שמתיו לך). It comes as no surprise that Esav now directs his bloodthirst for the hunt toward his brother, who must flee for his life.
Finally, in a desperate but doomed gambit designed to gain his parents’ approval, Esav marries from the family of Yishmael. But like so many young men, was too engulfed in his passions to make good judgments when it counted most. Even now, he doesn’t abandon his Hittite wives, but just adds a third on the sorry assumption that it will sway his parents back toward him.
The story of Yaakov and Esav is a story of two very different men. Each represents a different model of manhood, one more absolute and the other more moderate. Neither model of manhood is intrinsically better than the other, but each comes with strengths and weaknesses; opportunities on which to capitalize and blind spots and intense emotional needs to recognize and overcome; and, above all, a need to balance worldly accomplishment with inner cultivation.
All boys and men have a bit of Yaakov and Esav in us. The question is not what sort of man we are born, but what sort of man we become.