At the end of the first season, Chuck and Axe were continuing their mano a mano with Chuck tearing down the walls of Axe’s company in his search for a bug. Full of bravado, Chuck tells Axe that he’s the only man that can take on Axe, a guy with unlimited resources, because he has nothing to lose. It turns out this season that Chuck has a lot to lose, indeed. He is now separated from his wife, and his hands are full fending off the attorney general, who is out to torpedo his career.
To rub salt in the wound, Axe plans to buy every single copy of Winston Churchill’s first-edition autographed Second World War, a book that Chuck would give his eyeteeth to own. It’s not that Axe wants the book. He doesn’t. What he wants is to humiliate and break the beleaguered Chuck, screwing up Chuck’s career and his personal life as well.
Axe has already driven a wedge between Chuck and his wife by causing them to separate. Chuck can’t even have S&M with his wife anymore. No more black-leather masochistic sessions for Chuck. He is having a bad time of it, but he takes heart from what Churchill said: that you should never give up. Churchill’s words give him the strength to go on. Which is why he wants Churchill’s book so bad. Axe knows this and will do anything to keep Chuck from owning an autographed first edition of Second World War, no matter how much money it costs to buy every single existing copy. When his secretary tells him that’s going to be expensive, he boasts, “Then it’s a good thing I have a lot of money.”