In 1922, as a writer for the Chronicle, Jack is told to go to Mason City and look into Treasurer Willie Stark's crusade against corruption in a county schoolhouse building contract. Jack's editor assumes Willie's wife Lucy, a school teacher, is putting him up to the task.
Jack speaks with old men in town, who claim Willie wants to bring in black workers in supporting a low bid for the contract. At City Hall, Jack speaks with the County Sheriff and County Commissioner Dolph Pillsbury, treating both laconic, backwoods political figures with thick sarcasm. Jack meets with Willie (their second meeting, after the encounter at Slate's), who explains the situation: Pillsbury has a personal interest in ensuring that J.H. Moore, which did not put in the lowest bid, wins the contract. In trying to prevent this, Willie was slandered, with Pillsbury claiming that he supported the lowest bid, Jeffers Construction, which used Negro labor. There were two other bids, however, between the Jeffers and Moore bids.
Willie tries to convince the voters that he is right by using bland speeches and matter-of-fact tracts, yet they are uninterested in his case. Voted out of office, he retires with Lucy to his father's farm, where he diligently studies law.
Fatefully, the schoolhouse built by Moore, using bricks from a relative of Pillsbury, collapses after the brickwork gives way, resulting in three deaths and several injuries. As a result, Willie becomes a popular figure in the backwoods county, and eventually he "found himself running for Governor" (92).
Ex-governor Joe Harrison, whose support comes from the cities in the southern part of the state, essentially decides to put Willie up in order to split the vote with his opponent, incumbent Sam MacMurfee, whose support is from rural areas in the north. Tiny Duffy, an ally of Harrison, is sent to convince Willie to go ahead and manage his campaign.
On the campaign trail with Tiny Duffy and Sadie Burke, another Harrison operative, Willie delivers a series of meticulously written, dull, unmoving speeches. Jack covers much of the campaign, leading to several conversations with Willie in which the candidate bemoans the plight of his populist crusade, as well as a conversation with Sadie about her outfit's ploy. Once Willie realizes his campaign will fail, Sadie reveals the entire setup, gleefully taunting his naivete.
Willie, for the first time in his life, gets drunk the night before a big speech, and Jack administers more alcohol as a hangover cure the next morning to get him to the event, a large backwaters barbeque in Upton. There, Willie stumbles on the stage and, speaking off the cuff, reveals that he and his rural supporters had been duped, to the dismay of Tiny Duffy, who falls off the stage. Willie throws his support to MacMurfee and goes on the stump in his support, delivering a series of popular, fiery speeches in which he paraphrases insults from the politicians who had put him up to the affair: "Friends, red-necks, suckers, and fellow hicks" (132).
MacMurfee wins the race, and Willie goes back to private practice, retaining his popularity. In 1930, a new, more feisty Willie Stark wins election as governor. He selects Hugh Miller, a distinguished apolitical attorney equally intent on reform, as his attorney general, and he is willing to take Tiny Duffy, whom he mistreats, as well as Sadie Burke into his administration.
In that election, Jack leaves his job as a columnist after being asked to promote MacMurfee more forcefully. After this incident, he experiences a bout of prolonged idleness and sleeping, which he calls the "Great Sleep." Jack notes that this Great Sleep had taken place twice before in his life: after leaving his history PhD dissertation unfinished, and after his marriage to Lois began falling apart.
Unemployed during this period, Jack meets a few times with his childhood friend Adam Stanton, now a famous doctor and medical professor living in a shabby apartment in Burden's Landing. He also dines with Adam's sister Anne Stanton, another childhood friend, to whom is he clearly attracted. Anne shows concern for Jack's drifting in life as well his his hostile relationship with his father, Ellis Burden, who has been working at a mission and passing out Bible tracts.
At the very end of Chapter Two, Jack's Great Sleep is interrupted by Governor Willie Stark, now a more confident and arrogant man, who taps him for a job.
"I mean, what do I do for the job?"
"Hell, I don't know," he said. "Something will turn up."
He was right about that.
Chapter Two, a flashback covering Jack's past job as a reporter and the beginning of Willie's political career, charts the trajectory of Willie Stark's rise to power and his rapid evolution from the meek man Jack met at Slade's to the dominating politician showcased in Chapter One. Furthermore, the qualities of Jack Burden are more sharply defined, and more pieces of the past come to the fore.
The part of the chapter dealing with Mason City politics gives insight into Jack's views about other people. He sarcastically dismisses the simplistic politicians with whom he speaks.
They ain't real, I thought as I walked down the hall, nary one. But I knew they were. ... when they got old they lost their reasons for doing anything and sat on the bench in front of the harness shop and had words for the reasons other people had but had forgotten what the reasons were. ... Oh, they are real, all right, and it may be the reason they don't seem real to you is that you aren't very real yourself. (81-82)
Jack, an educated man, realizes that the petty affairs and corrupt officials in Mason City are irrelevant in the long run. He compares the politicians to the lethargic, idle old men on the bench, whose livelihoods have long since passed. Yet Jack is not "very real" himself insofar as to him, his own life contains a degree of meaninglessness.
Willie is shown as a moral, diligent, and intelligent man in the first part of the chapter. Whereas Dolph Pillsbury simply slanders Willie when accused of corruption, Willie uses a dull, honest plea; consequently, he is rejected by the voters and ignored by the local press.
At the start of Willie's political career, he is a realistic idealist. In his Mason County political fight, he tries to sway voters with dull statistics, hoping that they will find he is an honest man looking out for their best interests. After his landslide defeat, his photo is run in the paper with under the line, "KEEPS HIS FAITH." His idealism is bolstered by the fateful schoolhouse disaster that vindicates him, and he maintains his dull approach when campaigning for governor. Willie's transformation to a slick orator and political manipulator is sparked by the revelation that he has been tricked. After embarrassing Tiny Duffy and gripping the crowd with his fiery, drunken speech at Upton, Willie realizes the sheer power of manipulating the emotions of voters. From this point on, Willie understands the necessity of emotional appeal and wields crass showmanship and underhanded politics like the symbolic meat-axe he mentions in his later speeches. Thus, Cousin Willie becomes "the Boss," Governor Willie Stark.
The relationships among Willie and his underlings are forged in this chapter. Sadie Burke's sexual relationship with Willie takes root here. She helps him in his transformation by ridiculing his idealism and exposing him to the reality of politics. Sadie is used to latching onto strong male political figures, and she becomes inextricably close to Willie from this point forward. Tiny Duffy, who begins the chapter pulling Willie's strings, becomes his pathetic toady on whom the Boss heaps immeasurable abuse.
The relationship between Jack and Willie in this chapter is incredibly complex. At the start, Jack, the narrator, elicits few emotions towards cornpone Cousin Willie. He merely analyzes the stages of Willie's development. That is, he reflects on Willie's innocence, desperation, and naivete when he begins campaigning; he ponders the "luck" that tapped Willie to become a local hero after the schoolhouse collapse; then he watches quietly when Willie, partly through Jack's help, realizes has been duped, and when Sadie tears his ego to shreds. Willie confides his worries in Jack, who is just a reporter, when his campaign goes poorly. Even though Jack says little to boost Willie's ego, Jack, a flat character throughout this chapter, acts as a receptor for Willie's deepest fears and honest feelings while Willie undergoes his change. When Willie becomes governor, he recognizes Jack's honest steadiness and hires him. Jack treats Cousin Willie precisely the same as he treats Governor Stark. Throughout the novel, Willie confides in Jack, who never uses any of Willie's secrets against him, being fully withdrawn from politics. Willie can trust Jack, just as he can trust the loyal yet unintelligent Sugar-Boy; he cannot, however, trust any of his other subordinates, like Tiny Duffy, and he cannot have the same relationship with any of the women with whom he has affairs.
Jack's disinterested nature makes this relationship possible. In his job with the Chronicle, he is dispassionate about politics and willing to write articles slanted towards MacMurfee, whom the paper supports. His employment as a journalist ends when he is unwilling to add any passion to these articles. Jack's job with Willie will play out in the same manner; he is so dispassionate about politics and, indeed, other human beings, that he is willing to dig up dirt on anyone, even his close friends, for Willie to use to blackmail his opponents.
One more key aspect of Jack's character arises in this chapter. Jack is completely unambitious. Those around him, such as Anne, want him to do more with his life. Instead, he slips into long drags of the "Great Sleep," a manifestation of Jack's willful nihilism and powerlessness, if not depression. Jack's attitude contrasts strongly with Willie's extremely energetic idealism. Jack's lack of ambition stems from a variety of visible factors that are exposed in the coming chapters, including his failed love affair with Anne Stanton, his mother's divorce and subsequent frequent remarrying, and the departure of Ellis Burden, whom he believes to be his father, early in his life.