How did Bear react to Crispin's information in Chapter 44?

This episode indicates just how streetwise Crispin has become since teaming up with Bear. Previously, he was such a naive young boy, sheltered from the harshness of the big old world around him. But now, largely thanks to Bear's tutelage, Crispin has a much better understanding of the dangers that lurk round every corner.
The irony here is that Crispin is actually becoming more aware of those dangers than Bear himself. Though Bear is pleased with Crispin's eagle-eyed powers of perception—a sign of how well Bear has taught him—he doesn't take the threat from the one-eyed spy all that seriously. In turn, this means that Crispin has to become even more resourceful, surreptitiously following the strange man around to prevent him from doing any harm to his friend. The roles have been almost completely reversed; now it's Crispin who's looking out for Bear, rather than the other way round.

In chapter 44 of Crispin: The Cross of Lead, Crispin tells Bear that a mysterious one-eyed man, whom Bear made fun of several villages back, has been following the duo. Slightly paranoid, Crispin expresses concern with this man's presence and seems to believe they are in danger.
When Bear hears this news, he expresses pride in Crispin's cautiousness. He seems pleased that Crispin has learned to be on the look-out while noticing menacing figures like the one-eyed man. However, Bear doesn't seem to have any concern about the one-eyed man, and he promises Crispin that they will leave the village as soon as possible.
After Bear leaves for a meeting with John Ball, Crispin notices that the one-eyed man is once again following Bear; hoping to save his friend, Crispin trails Bear and the one-eyed man but loses track of both. After eavesdropping on Bear's conversation with John Ball, Crispin wanders the streets only to see the menacing one-eyed man with John Aycliffe approaching. Thus, Crispin's suspicions were correct, and Bear's lack of concern was naive.