Or HaChaim on Deuteronomy 1:36/אור החיים על דברים א׳:ל״ו

1 הוא יראנה ולו אתן את הארץ, "he will see it and to him I will give the land, etc." Why did Moses have to say that Calev would see the land seeing that he had been promised that G'd would give it to him? Surely just as 100 is part of 200, the land could not be given to Calev unless he was going to see it! I believe Moses wanted to recall two separate accomplishments of Calev in the matter of the spies and to show that he acquired two separate merits. 1) He separated himself from the advice of the ten spies and did not say a single negative word. 2) He was courageous enough to come out openly against the majority report asking the people to remain loyal to G'd, as we know from Numbers 13,30: "Calev silenced the people." As a compensation G'd granted Calev two good things. Concerning his initial silence G'd rewarded him by not letting him die as part of the decree which G'd decreed against the spies. This is alluded to in Moses saying: בן יפנה הוא יראנה, "the son of Yefuneh will see it." The meaning is that because he "turned away" פנה, he was granted the reward that he would see the land he had spied out. His peers had been specifically denied this, i.e. Numbers 14,23 where G'd said that the men of his generation would not get to see the land of Canaan. In reward for Calev having come out openly on behalf of G'd he was rewarded in that G'd gave him the land, i.e. he personally i.e. לו was allocated a share in the Holy Land.