The first one emerged red, all of him like a hairy mantle. They called his name Esav.

Be’er Mayim Chaim: Dovid is also described as being red – but not “all of him.” To the contrary, Dovid possessed “fair eyes and a pleasant appearance.” The ruddiness meant that like Esav, Dovid had a propensity to bloodshed. But he kept his eyes focused on law and propriety. He sought the counsel of Sanhedrin before launching a lethal campaign. Esav, however, was thoroughly suffused with bloodshed.

This is one hint among others about the nature of Esav. By describing him as emerging “first,” the pasuk alludes to his role as an iconic rasha. Evildoers, Chazal explain, are the “first” to be rewarded. By receiving their reward for their positive deeds in this world, they are left with nothing but tribulation for their misdeeds in the next, eternal, world. Esav, therefore, took pride of place in the race for olam ha-zeh. He beat out his younger brother in the enjoyment of this world.

Esav’s ruddiness can be an allusion not just to his involvement with bloodshed in general, but his readiness to inflict harsh judgment and bloody misdeeds upon the Jewish people. This trait of Esav would ensure that Yaakov would be a very distant second to Esav in enjoying any of this world; Yaakov as a people would take up the role of the tzadik who is denied the pleasures of this world, receiving his reward in the more significant world to come.

Esav’s lethal preoccupation with visiting suffering upon Klal Yisrael would liken him to a mantle of hair, i.e. he would find as many opportunities to cause suffering as there are hairs on a person’s head. He would cause so much pain so many times, that people would call him Esav, the one who is done, as if to say, “Enough is enough! Surely you are done! You have already caused your victims enough suffering!”

This reading of our pasuk might be the key to understanding a difficult midrash. ³

Chazal describe a Roman official demanding of R. Gamliel a prediction as to who will succeed the Romans in their hegemony. R. Gamliel took some blank paper and wrote, “…After that his brother emerged with his hand grasping the heel of Esav.” The Roman was impressed by R. Gamliel’s new take on an old thought. The midrash’s final word is that the incident underscores how much that tzadik would have to suffer.

Many have labored to explain this passage. Here is what it may mean: The length of this last, interminably long galus is set by our pasuk. Not only does Esav and his bloody campaign emerge first, but the back-story is even more somber. Esav represents the entire universe of evil and harsh dinim. All of it must “emerge;” before the final geulah, all evil must be wrung out of the fabric of creation, met head on, and subjugated by the powers of good. Evil is given its chance, but the din that animates it is tempered by its encounter with good, which causes its bitul, its negation. When that happens, Moshiach can preside over our geulah, as all the forces of good can emerge from the kelipos that previously contained them. The sparks of kedushah that lie dormant all over will emerge and shine powerfully.

While this is the scenario we might prefer, it works alongside a Plan B. Not only can teshuvah and mitzvos hasten the messianic redemption that will allow for the full display of the good that is now hidden, but the suffering and pain of galus also can bring this about. Think of Egypt, where the concentration of suffering within 210 years led to a shortening of that exile. People holding out against the evil thrown at them also demonstrates the emptiness, futility and ultimately the powerlessness of evil. HKBH in His mercy allows that the Plan B contribution take place over an extended period of time, which makes it more bearable than bearing down upon us in a way that we would find much harder to endure.

All of this is included in the image in our pasuk. The dinim, the harsh judgment brought upon us by Esav, sprout like hairs – slowly, so that we can survive them as a people, even if they are many. They keep coming, so that people look at Esav and cry, “Enough! You have already done to them everything that you sought, and they have survived nonetheless.”

R. Gamliel’s Roman interlocutor certainly knew about our pasuk, and knew of our belief in Moshiach. His intention was to trap R. Gamliel and torment him. Should R. Gamliel truthfully respond to his question and tell him that we would be the ones to next don the mantle of power, he would respond with righteous fury. He would use this display of confidence to inflict more harm upon the long-suffering Jewish people.

R. Gamliel avoided his trap. He took blank paper and wrote, i.e. he omitted the first pasuk, and began only with the birth of Yaakov. He deliberately made no mention of Esav as the vehicle for countless episodes of evil, of galus only ending after a slow, extremely long process.

Instead, R. Gamliel wanted the Roman to think that any excessive mistreatment of the Jews would be counterproductive, because it might set off the redemption implicit in the pasuk about Yaakov! R. Gamliel turned the tables on him. “Do as you wish with us! But realize that the more you harm us, the closer we will get to throwing off your yoke of oppression altogether!”

But as the midrash concludes – how much did R. Gamliel suffer in uttering the words that offered the Romans a license to do to us what they wished…