After twenty-two years in exile, Yaakov returns home. But before arriving back in Eretz Yisrael and confronting his brother Esav, a difficult challenge awaits him. Yaakov is called upon to fight against a most powerful opponent, and we – readers and students of the text – face the complicated task of trying to work out who this mysterious figure might be.

The most popular opinion among the commentaries is that it is an angel. But the Midrash does not suffice with this conclusion, and poses a most peculiar question: what was the angel’s appearance? The question is strange because an angel is not necessarily visible at all; it is a spiritual entity. Besides which, what does it matter to us how the angel looked? The entire subject would appear to be irrelevant. Nevertheless, the Midrash discusses the matter at length, offering no less than four different possibilities – all of which serve only to deepen our bewilderment. According to the Midrash, the angel appeared as a Torah scholar, as an idolater, as a shepherd or as a gang-leader.

What is the meaning of these images?

The key to understanding the Midrash would seem to lie in the Rambam’s teaching that some midrashim speak in parables: in other words, a midrashic answer must be understood as presenting a certain idea.

The “Iyun Yaakov” (a commentary on the legends of the Talmud) teaches that our midrash may be compared to another midrashic debate: whether the angel was the “captain” (guardian angel, as it were) of Esav, or the great angel Michael.

Let us follow this direction and attempt to understand the idea behind these midrashim.

The encounter with the mysterious adversary takes place the night before the fateful encounter between Yaakov and Esav is to occur. Yaakov must ready himself as best he can. What our midrash is debating is actually the question of how Yaakov should best prepare himself. If, according to one opinion, the angel is the captain of Esav – or, in the language of the other midrash, an idolater or gang-leader, then we are speaking of an external enemy, and the appropriate strategy involves trying to know this enemy, with all his strong and weak points, in order to be ready for any move that he makes in battle. Anyone who has been through military exercises is familiar with this sort of preparation.

But if Yaakov is engaged in battle against the angel Michael, then the picture is entirely different. Michael is the “captain” of Israel; he represents Israel- i.e., Yaakov himself. According to this view, Yaakov is not struggling against an external foe; he is struggling with himself. This is the meaning of the Midrash that teaches that his opponent is a Torah scholar or a shepherd.

Here the Midrash is proposing a conceptual alternative to this war. In order to prepare for battle against an enemy, one must first engage in battle with oneself. A person must scrutinize himself in order to come to know the strengths and weaknesses of his own character, of his own nation. Only after such scrutiny is he able to and justified in fighting against others.

The significance of these two approaches extends beyond Yaakov’s battle; they apply to every one of us at every stage of life. We must look outwards in order to know and evaluate our external enemies, but it is no less important that we also scrutinize and prepare ourselves inwardly, to know ourselves better.