Excerpts from Sicha, Shabbos Parshas Chukas 5750
A. Moses Sends Spies a Second Time
Forty years after the original episode of the spies, just before entering the Land, Moses sends spies to Yaazer. These spies—confident in Moses’ prayer—take initiative and successfully conquer the city (Source 1).
The Rebbe asks: How is it possible that the spies took on an additional mission of their own accord—one they were not commanded to do?
After all, the original sin of the first spies was precisely this: they went beyond their mission and drew their own conclusions (“We cannot go up”). If so, how could these spies to Yaazer also exceed the scope of their mission?
Since they were part of the “generation of knowledge” and were deeply connected to Moses, it must be assumed that their intentions were for the sake of Heaven. If the spirit of Moses within each Jew brings fear of Heaven to every Jew in all generations (Source 3), how much more so would Moses’ influence affect his own generation.
The explanation: the second group of spies came to rectify the sin of the first spies. True rectification must occur in the very area where the wrongdoing took place. Since the first spies overstepped their mandate in a negative way, these spies overstepped in a positive way—with trust in Moses’ prayer—and set out to conquer Yaazer.
B. The Tribes of Gad and Reuven Settle in Yaazer
Two tribes, who had much livestock, asked Moses for permission to settle in Yaazer and its surrounding towns. In the end, they received his approval (Source 4).
The Rebbe asks: How could these two tribes request to settle on the eastern side of the Jordan and not enter the Land promised by G‑d? This seems to echo the sin of the spies. The question becomes even stronger when we see that Moses agreed to their request.
The explanation: the tribes of Gad and Reuven certainly took care not to repeat the sin of their forerunners, the spies. On the contrary, they acted to correct it.
G‑d promised Abraham the land of ten nations, including the Kenite, Kenizzite, and Kadmonite (Source 5). However, when Moses spoke to the people, he did not mention the land of these three, because their conquest will only take place in the End of Days (Source 6). The intention of the tribes of Gad and Reuven was to settle the eastern side of the Jordan in order to hasten the fulfillment of G‑d’s promise to inherit the Land in its entirety. Unlike the first spies, who wished to remain in the desert in order to delay the inheritance of the Land, these tribes sought to settle the eastern side of the Jordan in order to accelerate the complete settlement of the Land.