Later on, according to rabbinic tradition, he was appointed to another fact-finding mission, as one of two spies sent by Joshua to check out the situation in Jericho (Josh. 2). Joshua knew how reliable he was and had no doubts that the reconnaissance would be unbiased.
Why the sages thought so highly of Caleb is partly explained by his piety. They surmise that when the twelve spies were in Canaan, the ten who later proved to be pessimists looked only at material aspects. Caleb, however, went to Hebron to find the graves of the patriarchs and to pray there for Divine guidance (Sotah 34b).
He was also loyal and fair to Moses. When the ten, the “evil congregation”, tried to provoke the people to rise up against Moses, Caleb stood up, listed all that Moses had done for Israel, and said, “Even if he were to tell us to make ladders and climb up to the heavens, we ought to follow him!” (Sotah 35a).
He has various names, and when he is described as Calev ben Yephunneh (Num. 13:6) it is a play on words, since he turned away (from the root panah) from the negativism of the ten pessimists.