Since G-d spared the firstborn Jews in the plague which hit the rest of the population, He asserted a type of special ownership over them, and commanded Israel to sanctify all their future firstborn to G-d.

But, this mitzvah applies not only to people, but also to kosher animals, and - surprisingly - first-born donkeys: "Every firstling donkey must be redeemed with a sheep" .

Why does this holiness of the firstborn apply to donkeys?

The firstborn holiness of donkeys is even more surprising when we consider that these animals are 100% impure. Some non-kosher animals, such as camels and pigs, have only one sign of impurity. Donkeys, however, carry both signs of impurity. The Zohar teaches that the donkey is "avi avot hatuma", the ultimate source of impurity.

In addition, 16th century Rabbi the Maharal of Prague noted that the Hebrew word for donkey (chamur) is the same root as the word for material (chomer). The donkey, he explained, is a symbol of crassness and physicality [Gevurot Hashem ch. 29]. So why did the Torah designate this ignoble creature to have the special holiness of bechor that must be redeemed?

Hidden Holiness

One explanation proposed by the Talmud [Bechorot 5b] is that the donkeys helped facilitate the Exodus as they carried the treasures of Egyptian gold and silver. Yet the Israelites could have used some other pack animal. It would appear that there is something special about the donkey, that it represents an inner truth about the redemption of the Jewish people, both in Egypt and in the future national rebirth of the Messianic Era.

The Israelites in Egypt had sunk to the lowest levels of immorality and impurity. Outwardly, they were indistinguishable from their Egyptian masters. Even the angels were unable to distinguish between the two nations. They questioned G-d's decision to save the Israelites at the Red Sea, protesting that the Egyptian army is no better than the Hebrews, "These are idol worshippers and these are idol worshippers!"

But like the donkey, the impurity of the Jewish people was only on the surface, hiding a great inner holiness. It was a superficial blemish, as it says, "Do not look upon me that I am black; for (it is only) the sun that has tanned me" .

Messiah's Donkey

We find a similar concept with regard to the future redemption. The Sages noted that the Messianic Era is described in conflicting terms. In Daniel's nighttime vision, the Messianic king arrives "with the clouds of the heaven" . The prophet Zechariah, on the other hand, speaks of a righteous king who makes his appearance as "a pauper riding on a donkey" . So how will the Messiah come - on heavenly clouds, or humbly on a common donkey?

Rabbi Yehoshua ben Levi explained that the form in which the Messiah will appear depends on us. "If they [the Jewish People] merit, he will come 'on heavenly clouds.' If they do not merit, then he will be 'a pauper riding on a donkey'" [Sanhedrin 98a]. In other words, if the Jewish people attain a spiritual level high enough, they merit a supernatural redemption with wonders and miracles. If, however, the redemption arrives because it is the final hour for its arrival - but the Jewish people are not deserving - then the redemption will come through natural means .

"A pauper riding on a donkey" is a metaphor for undeserved redemption without our merits, like the poverty of a poor man. It is a redemption based on natural processes, as exemplified by the donkey, a symbol of the material world. Yet this donkey, while externally crass and impure, has a special holiness hidden within - the holiness of the firstborn.

According to Rabbi Avraham Yitzhak HaKohen Kook, the Messiah's donkey represents the period of "Ikveta deMashicha," the generation leading up to redemption when its 'footsteps' (ikvot) are first heard. The Talmud [Sotah 49b] describes this era as one of terrible spiritual decline, replete with brazenness and immorality, falsehood and corrupt government. But the Zohar teaches that, despites its external faults, the generation will be "good on the inside." This inner goodness is reflected in the special souls of the pre-messianic era; despite the heavy darkness clouding their behavior and beliefs, they are blessed with an innate segulah or holiness, as expressed by their great love for the Jewish People and the Land of Israel.

The Function of "Chevlei Mashiach"

The Sages recognized the deeply disturbing nature of "Ikveta deMashicha," using the term "chevlei mashiach," the birth pangs preceding the Messianic Era. In his seminal work, Orot, Rabbi Kook discusses various reasons for the intense materialism and lack of spirituality that pervades the era of national revival. His central argument is that the Messianic 'birth pangs' come to correct an imbalance stemming from centuries of exile.

Rabbi Kook explained the process by way of analogy. The dregs in the bottom of the wine bottle are needed to preserve the wine. If a bottle lacks dregs, and we wish to correct the situation by adding dregs, the initial effect will be to muddy the entire bottle, temporarily ruining it. But as the dregs settle at the bottom of the bottle, the wine regains its clarity and benefits from the preservative powers of the dregs.

So too, the wicked and the base are needed to ensure the flow of normal life. The Exile, with its concentration on purely spiritual pursuits, weakened the life force of the Jewish people to such an extent that its national survival was endangered. The Jewish people needed to return to their land in order to survive as a nation. The return to the land and to a more balanced national life meant an increased involvement in the material side of existence. Initially, the crassness and brazenness of the pre-messianic era will cause great consternation. But as the negative forces are subdued, like the settling of the wine dregs, their alarming and detrimental aspects will be neutralized.

Transforming Darkness to Light

The "Ikveta deMashicha" is a trying time, and not all of the Sages were eager to experience it. Yet Rav Yosef showed great spiritual fortitude, saying, "Let the Messiah come, and may I merit to sit in the shadow of his donkey's dung" [Sanhedrin 98b]. Once again, the donkey metaphor.

Rav Yosef was accustomed to looking at the inner essence of things. He recognized the tremendous inner holiness hidden in this problematic generation, as symbolized by the Messiah's donkey. Rav Yosef understood that the Messianic light would demonstrate how to utilize all forces, even the most coarse, for the sake of good. He knew that the darkness of national rebirth would lead to an even greater light of Torah and knowledge of God.

[adapted from Igrot HaRe'iyah vol. II, p. 188, letter 555 (1913) ("Igeret Takana"); Orot p. 85 (Orot HaTechiyah sec. 45)]