Chapter Two begins in 1939 and soon shifts back to 1922 and to the first time Jack went to Mason City. He goes on behalf of the Chronicle to find out about Willie. Once there, he talks to old men outside the harness shop, Dolph Pillsbury and the sheriff. All demonstrate an inherent racism and tell Jack the problem with Willie is that he wants to accept the lowest bid on the building of the schoolhouse.
Jack visits Willie and discovers Lucy, his wife, has been sacked as a teacher because of the fuss and he (Willie) probably will not be re-elected as Treasurer as he attained the position through Pillsbury. He insists he will still run for election, though. Willie's version of events is that Jeffers offered the lowest bid for the building of the school, which is the one he favors. There were two other bids between this one and the one the others (including Pillsbury) want to accept, which is Moore's. Pillsbury uses racism as a defence for arguing against Jeffers as well as the belief he will bring strangers in.
A shift forward in time reveals that Pillsbury 'turned out to be Willie's luck'. The schoolhouse built by Moore was shoddily constructed. Three years after it was built a fire escape collapsed and killed and maimed children. Through this occurrence, Willie is proven to be the honest one. In this period, Willie trains to be a lawyer and is asked to run for Governor by the Democrats. Duffy is in league with the people who ask him to run and becomes his campaign manager. Willie is so complimented and awestruck by this offer that he fails to see he is being used as a 'sap', and Duffy does not tell him. Willie is being used to split the votes of one of the other candidates (MacMurfee).
Sadie inadvertently reveals to Willie that he is being used as a sacrificial goat and Willie proceeds to get drunk for the first time. The next day he gives a speech at a barbecue that had been pre-arranged. This time his speech is convincing as he does not use his notes full of figures. He calls Duffy a Judas Iscariot and tells the crowd he is pulling out of the election, but insists he will stand again. Willie goes on to campaign for MacMurfee, who is elected.
After working as a lawyer, Willie later stands in the Democratic primary and wins. Jack resigns from the Chronicle after the editor reminds him the newspaper supports MacMurfee (so he must too). Jack is unemployed after this resignation and falls into what he calls his 'Great Sleep'. This has occurred before, as when he gave up on his PhD and when his marriage to Lois was breaking down. He visits Adam and Anne Stanton in this period, and she is concerned for him and his relationship with his father, Ellis Burden.
The chapter ends with Willie, as Governor, offering Jack a job.
Chapter Two is useful for the more detailed portrayal of Willie's earlier life before power corrupted him. He is described as the honest man among many crooks and is punished twice for his naivety - as Treasurer and then for believing he is regarded as a viable candidate for Governor. This early incarnation of Willie as honest also exemplifies how a man can alter from good to bad. As demonstrated in Chapter One, once Willie is instated as Governor he employs similar tactics to those he had previously disavowed.