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Jack Burden describes driving down Highway 58 with his boss, Governor Willie Stark, in the Boss's big black Cadillac--Sugar-Boy is driving, and in the car with them were the Boss's wife Lucy, son Tommy, and the Lieutenant Governor, Tiny Duffy. Sugar-Boy drives them into Mason City, where Willie is going to pose for a press photo with his father, who lives on a nearby farm. The Cadillac is followed by a car full of press men and photographers, overseen by Willie's secretary, Sadie Burke. It is summer, 1936, and scorching hot outside.
In Mason City, Willie immediately attracts an adoring throng of people. The group goes inside the drugstore, where Doc pours them glasses of Coke. The crowd pressures Willie for a speech, but he declines, saying he's just come to see his "pappy". He then delivers an effective impromptu speech on the theme of not delivering a speech, saying he doesn't have to stump for votes on his day off. The crowd applauds, and the group drives out to the Stark farm.
On the way, Jack remembers his first meeting with Willie, in 1922, when Jack was a reporter for the Chronicle and Willie was only the County Treasurer of Mason County. Jack had gone to the back room of Slade's pool hall to get some information from deputy-sheriff Alex Michel and Tiny Duffy (then the Tax Assessor, and an ally of then-Governor Harrison). While he was there, Duffy tried to bully Willie into drinking a beer, which Willie claimed not to want, instead ordering an orange soda. Duffy ordered Slade to bring Willie a beer, and Slade said that he only served alcohol to men who wanted to drink it. He brought Willie the orange soda. When Prohibition was repealed after Willie's rise to power, Slade was one of the first men to get a liquor license; he got a lease at an exceptional location, and was now a rich man.
At the farm, Willie and Lucy pose for a picture with spindly Old Man Stark and his dog. Then the photographers have Willie pose for a picture in his old bedroom, which still contains all his schoolbooks. Toward sunset, Sugar-Boy is out shooting cans with his .38 special, and Jack goes outside for a drink from his flask and a look at the sunset. As he leans against the fence, Willie approaches him and asks for a drink. Then Sadie Burke runs up to them with a piece of news, which she reveals only after Willie stops teasing her: Judge Irwin has just endorsed Callahan, a Senate candidate running against Willie's man, Masters.
After dinner at the Stark farm, Willie announces that he, Jack, and Sugar-Boy will be going for a drive. He orders Sugar-Boy to drive the Cadillac to Burden's Landing, more than a hundred miles away. Jack grew up in Burden's Landing, which was named for his ancestors, and he complains about the long drive this late at night. As they approach Jack's old house, he thinks about his mother lying inside with Theodore Murrell--not Jack's first stepfather. And he thinks about Anne and Adam Stanton, who lived nearby and used to play with him as a child. He also thinks about Judge Irwin, who lives near the Stanton and Burden places, and who was a father figure to Jack after his own father left. Jack tells Willie that Judge Irwin won't scare easily, and inwardly hopes that what he says is true.
The three men arrive at Judge Irwin's, where Willie speaks insouciantly and insolently to the gentlemanly old judge. Judge Irwin insults Jack for being employed by such a man, and tells Willie that he endorsed Callahan because of some damning information he had been given about Masters. Willie says that it would be possible to find dirt on anyone, and advises the judge to retract his endorsement, lest some dirt should turn up on him. He heavily implies that Judge Irwin would lose his position as a judge. Judge Irwin angrily throws the men out of his house, and on the drive back to Mason City, Willie orders Jack to find some dirt on the judge, and to "make it stick."