In 1936, Jack mulls over the problem of finding dirt on Judge Irwin. He thinks the judge would have been motivated by ambition, love, fear, or money, and settles on money as the most likely reason he might have been driven over the line. He goes to visit his father, but the Scholarly Attorney is preoccupied taking care of an "unfortunate" named George, and refuses to answer his "foul" questions. He visits Anne and Adam Stanton at their father's musty old mansion, and learns from Adam that the judge was once broke, back in 1913. But Anne tells him that the judge got out of his financial problems by marrying a rich woman.
At some time during this period, Jack goes to one of Tommy's football games with Willie. Tommy wins the game, and Willie says that he will be an All- American. Tommy receives the adulation of Willie and all his cohorts, and lives an arrogant life full of women and alcohol. Also during this time, Jack learns from Tiny Duffy that Willie is spending six million dollars on the new hospital. Soon after, Anne tells Jack that she herself had lunch with Willie, in a successful attempt to get state funding for one of her charities.
Jack decides to investigate the judge's financial past further. Delving into court documents and old newspapers, he discovers that the judge had not married into money, but had taken out a mortgage on his plantation, which he was nearly unable to pay. A sudden windfall enabled him to stop foreclosure proceedings toward the end of his term as Attorney General under Governor Stanton. Also, after his term he had been given a lucrative job at American Electric Power Company. After some further digging, Jack extracts a letter from a strange old spiritual medium named Lily Mae Littlepaugh, from her brother George Littlepaugh, whom Judge Irwin replaced at the power company. The letter, a suicide note, reveals that the judge received a great deal of stock and the lucrative position at the power company as a bribe for dismissing a court case brought against the Southern Belle Fuel Company, which had the same parent company as American Electric Power. Littlepaugh says that he visited Governor Stanton to try to convince him to bring the matter to light, but Stanton chose to protect his friend the judge; when Miss Littlepaugh visited the governor after her brother's suicide, he again protected the judge, and threatened Miss Littlepaugh with prosecution for insurance fraud. After seven months of digging, Jack has his proof.
The information presented by this chapter is relatively complicated, but the actual structure of it is quite simple. Chapter 4 was the story of Jack's first great historical inquiry, into the Cass Mastern papers; Chapter 5 is the story of his second, into the history of Judge Irwin. Thus, aside from a few tangents about Willie, Tommy, Anne, and Adam, Chapter 5 is almost entirely occupied with the process of Jack's search, with how he goes about researching Judge Irwin's past. Jack thinks critically about the judge's character, and follows his conclusions through old newspapers and court documents; when he finally has the clues he needs, he uses money and psychological manipulation to obtain the final proof from Miss Littlepaugh.
Of course, in many ways the look into Judge Irwin's past is also a look back into Jack's own; the time Jack spends with the Scholarly Attorney and with Anne and Adam Stanton is telling. Jack's father (actually, Jack only thinks the Scholarly Attorney is his father; he will learn later that Judge Irwin is his real father) is intolerant and weak, mumbling Bible verses and refusing to answer Jack's "foul" questions. His dingy apartment above the Mexican restaurant is pathetic, as is his "unfortunate" George, who spends his time making angel sculptures out of chewed-up bread. Nevertheless, Jack feels a deep, almost secret yearning to be closer to his father. Recalling an episode from his youth, he remembers softly whispering, "Father ..." as his dad fed him chocolates. The Scholarly Attorney barely hears this and his inquiring response wakes young Jack from his emotional daze--he simply replies, "Nothing." This is one of our first clues that Jack possesses a somewhat ambivalent longing for connection with human beings, one that runs deeper than the cynical rapport he enjoys with Willie and the gang at the office.
Anne and Adam Stanton are important because they are the friends of Jack's childhood, and he feels effortlessly comfortable around them. Anne and Adam are much more enamored of their own past than Jack is, and deeply honor the figure of their father, Governor Stanton. To Anne and Adam, their father represents a moral ideal which they must constantly strive to live up to. This ideal shapes each of their lives. When they learn the results of Jack's inquiries--that Governor Stanton illegally protected Judge Irwin after the bribe--their lives will nearly be shattered.