This is where we are introduced to the character of Esav, the all-time baddie. The rabbis accuse him of violence, rape, murder, cruelty, and almost any crime you care to mention. We know that “Esav” or “Edom” was used in the Midrash and Talmud as a code for Rome, and they had plenty of good reasons to be anti-Roman at the time, given the aggressive way the Romans dealt with the Jewish insurrections.
But if you look carefully at Esav’s character as it appears in the Torah, he does not seem to be quite as bad as he is made out to be. It is true that he doesn’t seem to care about his birthright, but then most people when they are totally exhausted might want to revive first and think later. It is true that he threatens to kill Yaakov, but then there were extenuating circumstances. He is clearly upset when he does not get the blessing. He cries, hardly the response of a hard, bad man.
The case against Esav is that he is a man of uncontrolled impulse, a dissembler, and religious hypocrite. The very characteristics that Yaakov has, being calm and calculating, even single-minded, are qualities that suit leadership far more than emotional explosiveness.
One might think that the qualities that differentiate Yaakov from Esav would be the ones that the Talmud might have admired in Rome. The Jewish rebels seem to have exhibited the qualities of Esav rather than Yaakov. Based on the gemara in Gittin, they actually killed other Jews who disagreed with them, put violence above negotiation, and tried to bully their way over the wishes of the majority. And if you take Josephus’s version of Masada, they went in for mass suicides, against halacha.
But remember that most of the religious leaders at the time of the great rebellions against Rome were not in favor of violence. Like Rabban Yochanan Ben Zakai, they wanted accommodation because they saw Torah and spirituality as being more important than land and politics. It seems to me that those same lessons apply today.