What are the connotations of "Va'yahas Calev es ha'Am"?
Rashi, Targum Onkelos and Targum Yonasan: It is an expression of silencing (he hushed the people) so that they should hear what he had to say about Moshe Rabeinu. 1
Ramban: It means that he silenced them, by arguing that the Cana'anim may well be strong, but we are stronger than them and their fortified cities.
Seforno: He needed to silence the people, because they had already started to grumble, in reaction to the spies' words. 2
Rashbam: It means that he silenced them in his wisdom. 3
Seeing as the spies hd not yet completed their report, what prompted Calev to interrupt them?
Seforno: He needed to silence the people, because they had already started to grumble, in reaction to the spies' words. 1
Seforno: As they did in full in 14:1.
Why does the Torah adds the (otherwise superfluous) words "Vayahas Calev es ha'Am el Moshe"?
Rashi: Calev announced 'Is that all that ben Amram did to us,' 1 conveying the impression that he was about to list all the bad things that Moshe had done to them, and the people fell silent to hear what he had to say. He then continued 'He split the sea for us; He brought down the Manna and blew in the quails!' 2
Calev actually used the expression "Asah lanu ben Amram", which is ambiguous, and can mean either 'to us' (which is what the spies understood) or 'for us' (which is what he intended to talk about.
Seeing as the people had already been convinced by the spies, how did Calev get them to listen to him?
Ramban: By arguing that ?the Cana'anim may well be strong, but we are stronger than them and their fortified cities?. 1
Why did Calev succeed in silencing the people and not Yehoshua?
Sotah, 35a: Because, when Yehoshua tried to quieten the people, the other spies would not let 'that leader with his head cut-off' speak. 1
Oznayim la'Torah (on 14:24): Yehoshua remained silent, because he figure that the people would accuse him of being biased towards his Rebbe Moshe. 2
The Oznayim la'Torah suggests that this was due to the prophecy of Eldad and Meidad - Refer to 13:2:5.1:1 - based on which they argued that Yehoshua was biased and that he wanted to give a good report of the land only because he was destined to lead the people when they entered it. See Oznayim la'Torah DH 'va'Yahas Calev' #2. who elaborates.
See Oznayim la'Torah there, DH 've'Avdi Calev'.
What does the Pasuk mean when it writes "va'Yahas Calev es ha'Am el Moshe"?
Seforno: And presumably Moshe told them not to be broken and afraid, as the Pasuk writes in Devarim, 1:29.
What did Calev mean when he said "Aloh Na'aleh ... "?
Rashi: He meant that even if Hashem would instruct them to build ladders and ascend to heaven, they would succeed in doing so.
Seforno: He meant that they were certainly able to go up, because the ana'anim would not be able to stand against us!' 1
Seforno: And Calev said this to back Moshe's previous statement. Refer to 13:20:3:2*.
Why did Calev add the words "ve'Yarashnu osah", omitting any mention of fighting the Cana'anim and conquering the land?
