1. V'avdi Kaleiv eikev hay'sa ruach acheres imo... Sefas Emes asks why the Torah has to justify Kaleiv getting a portion in Eretz Yisrael. That should be the result m'meila, by default. It's only everyone else's wrongdoing which caused them to lose their portion.
Sometimes not doing wrong is not enough. When terrible evil is taking place, you have to step up to the plate and take action, take a stand, and let your voice be heard in opposition. Had Kaleiv simply remained passive and not done wrong, I think perhaps he still would have forfeited his portion in the Land. It's only by speaking out that he deserved it. (Sefas Emes gives a different answer.)
2. Rashi (12:3) explains that the term “anashim”, men of importance, is used with respect to the spies because they were righteous people and not sinners. Yet, Rashi later (12:26) explains that the spies already had their evil plan in mind when they departed, implying that they were wicked from the start. Which is it?
There is a well known chakira in Achronim with regards to how shlichus works: if Reuvain appoints Shimon as his agent, does that means that it's as if Shimon becomes Reuvain, and everything done by Shimon is as if Reuvain was doing it, or does it simply means that the **result** of Shimon's action is attributed to Reuvain, but Shimon himself is an independent actor?
Maharal in Gur Aryeh uses the first tzad of the chakira to explain Rashi. The spies who were selected were in fact righteous people. However, once they were selected as shluchim by the tzibur, shlucho shel adam k'moso, they became the tzibur. Klal Yisrael unfortunately did not have the right motives in mind in sending meraglim, and therefore, once appointed, they became tainted by that identification and took on the tzibur's bad character.
We've done this Maharal in a previous post, but I bring it up again to have an excuse to share the Ohr Sameiach's (Geirushin 2:15) beautiful proof to the second tzad of the chakira. The gemara (Temurah 10) raises the question of whether it is the person who brings a korban or whether it is the person for whom the korban serves as a kaparah who can make temurah with it. The gemara proves that it's the latter: the Mishna says that a tzibur or shutafim cannot make temurah. Why not? If the tzibur or shutafim appoint a shliach to bring the korban on their behalf, then the shliach should be able to make temurah with it as he is an individual. QED that it's the person who is getting the kaparah which is the key, and it is still the tzibur/shutafim who are getting the kaparah.
Says the Ohr Sameiach: according to the first tzad of our chakira in shlichus -- Shimon the shliach becomes Reuvain -- then the shliach of the tzibur/shutafim should be no different than the tzibur/shutafim themselves. It's only according to the second tzad -- Shimon the shliach is an independent actor the result of whose deeds are ascribed to Reuvain -- that the gemara makes sense.
Pretty convincing. Amazing bekiyus. It's the Ohr Sameiach after all.
3. The Zohar writes that the meraglim did not want to enter Eretz Yisrael because in the midbar they knew they were the "rosh," but that status would be lost once they entered the Land. We are talking about the best and brightest leaders of the best and brightest generation in Jewish history -- did they really selfishly sabotage everything just to retain their own power?!
Shlucho shel adam k'moso. Sefas Emes (5639) explains that what made the meraglim leaders into the "rosh" was the fact that they represented the "rosh" of Jewish history, a spiritually elite. You want such a generation, they thought, to sacrifice their spiritual bounty and take up growing Jaffa oranges? Farming, building, conquering? What kind of job is that for a nation of kollelniks? It was not protecting their own interests, but rather protecting the spiritual status of their generation which motivated the meraglim.
In a nutshell, the meraglim thought holiness could only be cultivated in the protective bubble of the desert, surrounded by the ananei ha'kavod, sustained by the man and the be'er. The reality is that holiness can be found everywhere -- the more mundane the environment, the greater the kiddush Hashem in sanctifying it and revealing the kedusha found there. That's why we are put in a physical, mundane world. That's why we have to farm, to build, to conquer.
Many meforshim read the parshiyos that follow the cheit ha'meraglim as a response to their error. Rav Teichtel in that vein has a wonderful derush on the pasuk that introduces the mitzvah of challah, "V'haya b'achalchem mi'lechem ha'aretz tarimu terumah la'Hashem." (15:19)
The Tur (208) writes that when one says a bracha mei'ein shalosh, one should omit the words "v'nochal m'pirya v'nisba m'tuva," as there is no inherent value in just enjoying the fruit of Eretz Yisrael. The gemara rhetorically asks, "Did Moshe Rabeinu want to enter Eretz Yisrael just to eat its fruit?" Bach disagrees. He writes that the fruits of Eretz Yisrael are nourished by the Shechina itself, and by eating, we connect with G-d. (See post here.)
"V'haya b'achalchem mi'lechem ha'aretz," when one is not eating man -- when instead one is eating mundane bread, created from the wheat grown and harvested by our secular labor, "tarimu terumah la'Hashem," that is an opportunity to elevate that work, that meal, that food, and discover within it something holy to Hashem. (See Sefas Emes 5641 as well).
4. P.S. The Seforim blog has a fascinating piece looking at some of the material from the archives of R' Herzog's letters, now available online. Link and link. Well worth your time!