In the episode, "Undefeated," a rival law firm named Wakefield Cady offered him a junior partnership if he leaked the witness list. He accepted because he had huge law school debts. He went to the firm's IT technician Benjamin and posed as Louis to get Rachel's employee code (although he didn't know it was her code). He then sent the list under Rachel's identity. However, after he gave them the list, Wakefield Cady rescinded the offer. When Mike found out, he gave Jimmy two options to clear Rachel's name: either to own up to his deed and most likely get fired or else to let Mike turn him in, which would hurt his reputation and follow him for the rest of his career. Jimmy then resigned from Pearson Hardman.
He is seen again in episode "Blood in the Water", when met Mike in bar. He told Mike that he is not angry anymore, but thankful because Mike gave him "a lecture" and second chance. Then he promised to return the favor and suggested Mike to work for Bratton Gould. Jimmy helped reveal that Bratton Gould was taking associates and clients from Pearson Hardman. At the end of the episode, Mike asked Jimmy to recommend Bratton Gould hire Harold Gunderson, who had been recently fired by Louis.
In "Self Defense", Mike contacts Jimmy and asks him to lie in court and testify that he remembers that Mike went to Harvard. Jimmy refuses to perjure himself and risk prison for Mike, even when Mike brings up Jimmy's aunt, a settlement case Mike had done as a favor to Jimmy. However, JImmy later shows up to trial as a rebuttal witness and testifies on the stand that he was classmates and friends with Mike at Harvard.
- As described himself he "came from nothing" and worked really hard to get into Harvard Law and become associate.