Why did Moses send spies who were leaders?

Question

In Shelach Lecha, Moses, at the behest of the people, sends out twelve high ranking people to spy on Canaan. As we know, this wasn't such a success.

Thirty-nine years later, Yehoshua (Joshua ch. 2) sends out two unnamed people (maybe there's a midrash that gives them names, but there's none in pshat). That worked out fine.

If I were sending a spy, I'd try to send someone unknown. I would never send, e.g., a governor or congressman, to spy on another country, but rather a random person who won't attract attention. Why did Moses choose to send famous leaders? Conversely, why did Yehoshua choose to send (literally) no-names?

Answer 1

There is a difference between Moshe's intention in sending spies and Yehoshua's intention.

Moshe's intention was to persuade the people and "boost their confidence" so that they should be willing and ready to enter the land without complaint. He wanted spies that would scope the land and its inhabitants and return to tell the people, who would listen to and be influenced by their judgement, that the land was beautiful and the cities were conquerable with the help of God. For this reason, Moshe chose influential members of the community, "ראשי בני ישראל".

Yehoshua was not interested in influencing the public opinion. He was interested in information that would help him make strategic military decisions. He wanted to know the culture and the mindset of the inhabitants of Canaan. He wanted to know how the cities were oriented, their level of defense etc. For this reason, the spies' standing in the community didn't matter. They weren't going to make any public statements; they were going to report back to Yehoshua directly. No need for twelve spies so that all the tribes would listen. Yehoshua was the only one listening.

Why wasn't Moshe interested in military information? (Well, he was to an extent, but only insomuch as it would influence the public to show they could defeat their enemies.) Malbim attributes this to the fact that Moshe led al pi nes; he led the people miraculously. Had he led them into the land, military strategy would have been irrelevant. He was trying to boost people's confidence, their trust in God, to be worthy of His miracles. Yehoshua, on the other hand, led al pi teva, a natural leadership. (Not to say that he could never perform miracles. He surely did.) Military information was necessary for him to succeed. Thus he sent out spies to gather information.

Answer 2

Perhaps indeed for this reason, Rashbam (13:2) understands the phrase כל נשיא בהם to mean simply "from among those who volunteer (נשא אותם לבם) for this mission." Such people would, of course, have been strong and fearless types, but it is quite possible that they were unknowns up to this point.

Following the usual explanation, that they were indeed leaders, though, Ramban explains that Hashem hoped that they'd then reinforce each other and prevent each other from succumbing to defeatism.

Sforno points out that to some extent this hope was indeed realized: all twelve of them agreed that it was a good land (13:27 and Deut. 1:25) - whereas lesser people might not have recognized its advantages. [The problem began only when ten of the spies claimed that it was unconquerable, thus demonstrating a lack of faith in Hashem - which didn't last very long; the next day, after Hashem's stern rebuke, the Jews' trust in Him reasserted itself (13:40ff and Deut. 1:41ff), just that by then it was too late to undo the chillul Hashem that had been caused.]