Why Was the Torah Revealed Outside of Israel?
The question itself leaves us perplexed and humbled. Ostensibly, the situation is backwards. If Israel is the Holy Land as described in the hallowed words of the Torah, why would the Holy Word itself not be revealed at the pinnacle historical moment: the arrival of the Israelites into the prophetic Promised Land? Wouldn’t the fate and destiny of the Israelites be derived from happenings in their ancestral spiritual home? 
One might suggest that the inhospitable desert was a training ground — a testing platform — to prepare the Jewish people for the rigors they were about to accept. Likewise, at a more basic level, it was used to confirm and reassure that they were indeed worthy to take up the sacred mantle of Torah law. One might suggest that, in addition to enduring the harsh terrain of the perilous desert, they needed to be free of the harsh cultural influences they absorbed while in Egypt and that they would encounter again in the Land. This new lifestyle and perspective — radical in scope, intimate in nature — would surely have been appropriate to inculcate once in the Promised Land.
What, then, is the ontological reason for this perplexing situation? Perhaps, we are learning that Torah is, at its core, more universalistic than particularistic, where it’s transmission and internalization is inherently valid to all peoples. Or perhaps, the giving of Torah to Moses on Mt. Sinai was a gift to the last generation of Hebrew slaves, contingent upon accepting that their plight in Egypt is truly at an end, while still accepting that leaving Egypt was a traumatic experience; before this generation ceded its authority to the next one, it was vital that they all could joyfully accept Torah and the next generation of Israelites could then adopt this holy writ fulfilling the legacy within the borders of their ancestral home.
I’d like to suggest three additional perspectives. The first is based on a midrash that shares a profound Jewish teaching on pluralism:
Why was the Torah not given in the land of Israel?…To avoid causing dissension among the tribes. Else one might have said: ‘In my territory the Torah was given.’ And the other might have said: ‘In my territory the Torah was given.’ Therefore, the Torah was given in the desert, publicly and openly, in a place belonging to no one. To three things the Torah is likened: to the desert, to fire, and to water. This is to tell you that just as these three things are free to all who come into the world, so also are the words of the Torah free to all who come into the world (Mekhilta B’Chodesh 5).
To that point, no one faction of Judaism — a sad phrase to articulate in itself — can ever own the entirety of Torah. By revealing the Torah in an ownerless zone, no one can ever claim that they are the true inheritors and authorities. The Torah is revealed in the desert to teach us that we all are equal owners and guardians of the tradition.
An additional approach is to consider the relationship between religious institutions and state, and the corresponding role of religion and broad sovereignty. Consequently, the Torah is revealed in the diaspora to teach that Judaism transcends statehood, sovereignty, or even a physical land to survive. The last two thousand years proves that. It can be understood then that revelation outside of Israel disseminates the deeply powerful pull of Judaism’s intellectual breadth and fortitude in the face of endless persecution. The humble person of Jewish faith knows that their ancestral rights are not bound to the whims of governments and feckless empires, but by a contract that extends into the heavens and beyond. It is clear that Torah can, and must, exist separately from the flawed sovereignty of humanity; Torah has the ultimate power to inspire and educate, but not control or dictate.
Rabbi David Hartman shared a thought-provoking analysis on this view: 
I give preference to the midrashim that imply that the covenant was made in the desert to teach the community that Judaism as a way of life was not exclusively a function of political sovereignty. We were born as a people within the desert in order to understand that the land must always be perceived as an instrumental and never as an absolute value. The memory that the covenant was made in the desert prevents us from falling victim to the idolatry of state power (A Living Covenant, 282).
Lastly, we can take a mussar approach to understand our question. Though we are “Chosen People,” we are not superior to any other race or creed. We are placed upon this Earth to be symbols for justice and peace. The Torah could have been revealed nowhere else but outside the borders of the Holy Land, in the humble desert. This was a deliberate choice, a pedagogical tool for the Jewish people: we are to walk in this same humility so that we do not force change upon others by way of sword.
Rabbi Yerucham Levovitz wrote:
Why was the Torah given in the wilderness at Mount Sinai and not in the calm and peacefulness of Israel? This is to teach us that true peace of mind doesn’t come from physical comforts, but from an awareness of one’s ultimate life goals. When you focus on this, you are constantly traveling toward your goal and will never be overly disturbed or broken.
Indeed, had the Torah been revealed within the beautiful calm land of our destiny, we might have credited the external land for our inner peace. Rather, we needed to learn that peace is achieved internally. The Torah transforms our inner being and that can even happen in the chaotic barren desert.
Ultimately, we may never know the true reason why the Torah was given outside of Israel. The notion of a heavenly presence coming down to Earth, goes beyond our temporal understanding. What we can discern from our sages, however, is that there are manifold meanings in such a divine action and that each has its own relevance. As we yearn to seek the truth of the universe, we can look back to our ancestors and see what they went through to accept the words of Torah into their minds, their souls, their hearts. It is our task to see that their holy journey is continued and made relevant for eons to come.
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Rabbi Dr. Shmuly Yanklowitz is the President & Dean of the Valley Beit Midrash, the Founder & President of Uri L’Tzedek, the Founder and CEO of The Shamayim V’Aretz Institute and the author of nine books on Jewish ethics. Newsweek named Rav Shmuly one of the top 50 rabbis in America.