It is in Chapter 18 that Bear confronts Crispin as he tries to steal Bear's bread. However, initially at least, it is clear that Bear is a terrifying figure to Crispin and he does not agree to help Crispin so much as make him swear to serve him and to be Bear's servant. Bear only helps Crispin as their journey continues and he learns more about Crispin's life and makes some deductions, but even then he deliberately keeps Crispin in the dark about his identity for his own protection. In Chapter 18, however, it is clear that Bear, although he is probably feeling sorry for Crispin and his hunger on some level, is definitely a figure who only terrifies Crispin. Note for example what he says after Crispin has vowed to serve him:
"Done," he proclaimed. Then he put his dagger aside and tossed me a piece of bread. "Now you are mine, or God will chew you up and spit you out like the living filth all wolf's heads are."
It is clear that thi speech does not reveal Bear, at this stage, to be the kind, loving man that the text eventually reveals him to be later on. Rather, at the beginning of their relationship, Bear is a figure of terror for Crispin, and a man whom he suspects is actually mad because of his views about freedom and slavery.