The rabbis (Bava Batra 16b) identify the wording of Yishmael’s death as a sign that he died a righteous man. Allaying qualms about questionable behavior alluded to earlier in his lifetime, they say that we see from the burial of Avraham that Yishmael did teshuva (repented): Comparing this burial to Yitzchak’s later on, they notice that Yishmael allows his chosen younger brother to precede him, something which Esav does not.
The obvious implication is that Esav remained evil, even at his father’s funeral. Yet there are qualifying circumstances why Esav would not be so quick to forego the honors normally falling to the firstborn. R. Yaakov Reischer notes the most obvious in his commentary, Iyun Yaakov: Yishmael is born of a mother of lower status than is Yitzchak, whereas Esav and Ya’akov are of equal birth. In addition, Yishmael had been expelled from Avraham’s home, making his own status – not to mention his relationship with the father he was burying – more tenuous still. By ignoring these two factors, the rabbis may be saying that they are ultimately irrelevant. That is to say that both Yishmael and Esav knew that their positions of honor had been displaced with their fathers’ and – ultimately – God’s consent. The choice to ignore this was open to both, but chosen only by Esav.
In spite of the above rabbinic verdict, it is obvious that Yishmael had fewer obstacles in recognizing his brother’s position. Since his mother’s status and his history would have made it difficult to present himself as a pretender, it was certainly less of a challenge. Divine reward and punishment is meted out individually precisely for such reasons. Faced by the exact same situation, what may be an almost impossible test for one person will be easy for someone else. Be that as it may, these crossroads come with certain natural consequences. If Yishmael had an easier time passing the test, it nonetheless placed him where he needed to be.
Something worth noting is that what made Yishmael’s path to righteousness easier were things that made the actual course of his life more difficult. Being the heir apparent into early adolescence, only to be replaced by a new child born of a mother who was the nemesis of his own, could not have made for an easy life. That this culminates in being thrown out of his father’s home must have been nothing less than traumatic. Indeed, Yishmael’s challenge was whether to come back at all. Having been so clearly rejected, why would he want to have anything more to do with his father? Some sources soften this by suggesting that Avraham went to visit Yishmael and keep abreast of his welfare. Others posit a reconciliation after Sarah’s death. Regardless, there is no doubt that Yishmael had endured much. While Esav had his own issues, they paled in comparison. Losing the blessing that he coveted to his brother clearly threw him. But he was still able to get some sort of blessing from his father. Nor was there any indication of being disinherited. In fact, he must have been at least somewhat consoled by the fact that it was not he that had to go into exile, but his brother, Ya’akov.
It is hard to know if Yishmael would have preferred Esav’s relatively easier lot. Yet it is precisely Yishmael’s difficult circumstances that benefited him greatly. They prepared him to come to grips with his predicament and move on. The end result of this is that the Torah recognizes him as a righteous man, an honor shared by a very select group of men. That this honor could have been shared by Esav is underscored by the Midrash (Shir HaShirim Zuta 1:13) who groups him with what it calls the greats, only to inform us that he is the one who took himself out of this select group. Unfortunately for him, it was this very potential that ended up backfiring and preventing him from humbling himself and accepting his younger brother’s superiority.
Many of us have difficulty not looking with envy at those who seem to have it easier. Whether it is regarding finances, family or more lofty matters, we wonder why others have been given so much advantage. The story of Yishmael and Esav, however, shows that we need to be careful about that which we wish for. For it is quite often the advantage we wish we had that is the very undoing of others.