When jane first met Bob, he looked at him suspiciously and asked him I f he knew him. Bob answered by saying that he knows him. And then they shook hands and there was kind of an emphasis on that handshake. The following episode , jane learns that he shook hands wiyh red john. Also in the 99th episode we can see bob kirkland talking to the head of the fbi telling her to talk to the head of the cbi to keep updated on janes work in the red john case