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According to the Rosh (Rabbeinu Asher, Yevamot 64a), even Avraham Avinu may have faltered here. Avraham was in the Land at age seventy but later left, requiring Hashem to command him again five years later: "Go forth from your land." The Midrash similarly teaches that many Israelites preferred remaining in Egypt, even in slavery, rather than journeying to the Promised Land. Most perished during the plague of darkness. Yet remarkably, even those who left Egypt repeated the same mistake in the episode of the spies.
Even after failing twice, G-d had to surprisingly urge Yehoshua to bring the people into the Land despite their reluctance (Rashi Devarim 31, 7). The pattern resurfaced in the days of Ezra and Nehemiah, when the majority of Jews, including many leading figures, chose to remain in exile rather than return to rebuild the Second Temple (Yoma 9b).
Throughout Jewish history, prominent rabbis such as the Ya'avetz, the Vilna Gaon, and the Ohr HaChaim lamented that even Jews who were meticulous about other commandments often neglected the mitzvah of settling the Land of Israel, a mitzvah described by the Sages as "equal in importance to all the others combined" (Tosefta, Av.Z. 5, 2).
R. Yehudah Halevi's Kuzari (ii, 24), when challenged about his personally living outside the Land, the learned rabbi admits: "Indeed, you have found the source of my shame." Likewise, Rabbi Joseph B. Soloveitchik, despite criticizing American Jews for not making Aliyah ("Kol Dodi Dofek"), openly confessed his own failure to do so, acknowledging his sin towards Eretz Yisrael & personal blame without excuse (Ish Al HaEdah, p. 251). Rabbi Yissachar Teichtal, in Eim HaBanim Semeichah (p. 167), similarly describes a puzzling indifference—and even opposition—to the Land among respected rabbinic leaders in Europe.
One might have hoped that the final and eternal return to Zion would be different, that Jews would finally make Aliyah joyfully. Yet the Sages already warned (Rashi, Dvarim 30, 3) that the ingathering of the exiles would be extraordinarily difficult, as though God Himself would need to "drag" each Jew individually home to Israel.
The answer to this constant weakness, I believe, lies in a deeper understanding of the spies, ourselves and the Land.
The rabbinic midrashim apparently present contradictory portraits of the spies. 1 One source describes them as righteous men when they departed; another claims they were already corrupt. Kabbalists explain that they preferred the spiritual atmosphere of the wilderness, where they could devote themselves to Torah study without worldly concerns. They feared that life in the Land would require engagement with work, army, politics, and material reality. But other sources suggest the exact opposite: that they preferred the comforts of ordinary life and were intimidated by the intense spiritual demands of the Land of Israel.
Even the famous giant fruits of the Land are interpreted differently. Some traditions say the 10 spies brought them to emphasize the Land's excessive materialism, while others maintain that Yehoshua and Calev brought them to demonstrate that the Land excelled not only spiritually but also materially.
These conflicting traditions point to two OPPOSITE fears. Some viewed the Land as too physical; others saw it as too spiritual.
I recall from my non-Zionist relatives who avoided Aliyah claiming Israel was too secular, while conversely, many secular Jews avoided it because it was the "Holy Land" and therefore, in their minds, belonged to the religious! In short, the Land of Israel often "falls between the cracks," so whatever one's outlook, one can find a reason to reject her!
The deeper truth, however, is that the Land of Israel embodies a unique harmony between the spiritual & physical. Here, the sacred and the mundane are not enemies but partners. A physical land but also holy.
This, I believe, is both the CHALLENGE and the SECRET of the Land of Israel. Its uniqueness lies precisely in its ability to unite heaven and earth. It testifies that there is one Creator who fashioned both this world and the next, the sacred and the ordinary. In such a place, even figs and stones possess holiness.
The punishment of the spies is now obvious. Those who fail to appreciate the Land's complexity and harmony, by simplistically seeing either black or white, and pessimistically focusing just on what they DON'T want, are simply unprepared for it, and will inevitably not make Aliyah, doomed to stay in the exile.
Only the partnership represented by Yehoshua and Calev (the positive spies) provides the proper perspective: Yehoshua, from Ephraim, associated with practical nation-building; and Calev, from Yehudah, associated with spiritual leadership. Together they embody the religious-Zionist synthesis necessary to understand the harmony and secret of Eretz Yisrael & monotheism.
Rabbi Ari Shvat (Chwat)
^ 1.
ב"ר טז, ה, מובא ברש"י, במדבר יג, ג; סוטה לה ע"א; ראו מגן אברהם, או"ח תקפ, ב; מהר"ל בחידושי האגדות על סוטה לד ע"ב; פירוש עקידת יצחק; שפת אמת, פ' שלח; זוהר, קס ע"א.
ב"ר טז, ה, מובא ברש"י, במדבר יג, ג; סוטה לה ע"א; ראו מגן אברהם, או"ח תקפ, ב; מהר"ל בחידושי האגדות על סוטה לד ע"ב; פירוש עקידת יצחק; שפת אמת, פ' שלח; זוהר, קס ע"א.
Rabbi Ari Shvat
Lectures at various yeshivot, michlalot and midrashot. Has published many books & Torani articles and is in charge of Rav Kook’s archives.

Ein Aya Why Judaism Respects the Corpse and the Dead- Eternity, Not Superstition
Ein Aya Shabat Chapter B Paragraph 52

Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
Lessons
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Kuzari -Rabbi Ari Shvat Kuzari class 9 - "Seeing is Believing" (parag. 21-30)
These paragraphs elaborate on the theme that seeing and knowing is better than any attempt to prove logically, and begins explaining the difference between Israel and gentiles.

Ein Aya Various Universal Stages of the Geula Process
Rav Kook examines the various stages of redemption, explaining how (in addition to the obvious oft-mentioned stages of ingathering the exiles, reviving the Hebrew language, army, state etc.) the messianic dream of world prosperity, the State of Israel and world unity can and are realistically and logically gradually coming true.

Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
How do we know that the "claim" of mass revelation to 2,000,000 witnesses at Mt. Sinai is really true? This important class answers all of the questions skeptics ask about this claim of the Kuzari.

Ein Aya Armies Still Necessary for Balance & the War Against Wars
Rav Kook explains why the world was originally divided into the various seemingly contradicting ideologies and cultures, in order to develop each one respectively. Swords or armies symbolize how each respective ideology defends themselves, as well as deters their opposing ideologies and cultures. On the other hand, the messianic era will be one of peace, and Rav Kook explains the transition to that stage, which mankind is already undergoing.

The Land of Israel LGBT'S IN ISRAEL
The question was asked, how can one make Aliyah with the LGBT parades?

Kuzari -Rabbi Ari Shvat Kuzari class 7 - Five Accumulative Proofs of G-d
As a preparation for the Kuzari's classic proof of G-d from the mass-revelation at Sinai, we start here with 5 other directions to strengthen our belief which also contribute to what the Kuzari will present as well.

Ein Aya Muscle & Meaning: The Dual Nature of Gevurah (Physical Strength)
Is physical strength and fitness a necessity or an ideal? Although it if often totally overlooked among topics of Judaism, Rav Kook writes that it clearly is also a necessity to deter the many enemies of Israel, but even in Y'mot HaMashiach, in the Messianic era, to a certain extent, it's ideal continues even after our enemies will have been finished off.








