Back out in the cold, Jurgis realizes that changing his hundred-dollar bill will prove difficult. He knows that the bill will arouse suspicion in the hands of a "bum" like him, and he fears getting robbed or arrested because of it. In spite of these concerns, Jurgis tries to get change at a saloon. The dubious bartender makes Jurgis buy a five-cent beer first, and gives Jurgis only ninety-five cents in change for his hundred-dollar bill. Jurgis is furious, and assaults the swindler, but the bartender knocks him down. The police arrive, and Jurgis is taken in to custody.
For the first time in a while, luck has been on Jurgis's side. But despite this miraculous windfall, the world is still stacked against Jurgis. Even when Jurgis has a sudden windfall of money, there is no way he can actually access it. He is easily stripped of it through deception, and he is largely powerless to regain the money that has been stolen from him.
Jurgis stands trial. The bartender gives his version of events, which depicts Jurgis as a delirious, violent drunk. The haggard Jurgis then tells his story, which the judge finds preposterous. Jurgis is dismissed as a lying alcoholic and sentenced to ten days in prison, plus the costs of his jailing. It is later revealed that the saloon owner regularly bribes the police, and that the bartender is a crooked henchman of a Democratic party leader.
Jurgis's extraordinary luck in receiving the hundred-dollar bill is no match for Chicago's absolute corruption. The police do not serve justice; they serve money, the people who pay them off. Meanwhile, the judge's dismissal of Jurgis's story shows how the system—the one which made him poor—sees his poverty as showing that he should be poor and acts suspiciously to the possibility that he might have money. In other words, justice is blind to the corruption in its midst, or, even worse, sees the poor as the source of that corruption.
At Bridewell prison for the second time, Jurgis reunites with Jack Duane by chance. After talking with the other prisoners, Jurgis decides to support himself through crime. When he is released from prison, Jurgis seeks out Duane. The two team up and mug an insurance salesman; Jurgis nets fifty-five dollars for himself. Later, Jack and Jurgis read about their crime in the newspaper: their victim suffered a concussion, lay in the freezing cold all night, and may lose three fingers to frostbite. Jurgis is remorseful, but Duane convinces him not to feel bad.
Because judges, police, and businessmen don't seem bound by the law, Jurgis can't see why he should be, either. However, as he begins to adopt the dishonesty of the people who swindled him, he also begins to lose the moral uprightness that differentiated him from his corrupt surroundings. Jurgis's morals have become a casualty of a broken system, showing how that system in some sense pushes people toward immorality as it seems like the only way to survive.
Jurgis's partnership with Jack Duane gives him a glimpse into the big-time Chicago underworld. Chicago is controlled by crooked businessmen, and millions of dollars change hands to rig elections and bribe functionaries. This so-called "graft" system governs the interactions between law enforcement and criminals—who are often one and the same. Jurgis is taken aback by how freely money flows in this criminal underground, and quickly builds a name for himself as a trustworthy and dependable accomplice. These connections allow him to circumvent the criminal justice system in the same way as crooks like Phil Connor did. In the meantime, Jack Duane is caught breaking into a safe. A crooked policeman lets Duane escape from prison, but the escape is such an outrage that Duane's associates sell him out in order to protect themselves, and Duane is forced to leave town.
Jurgis's venture into crime shows him that Chicago's industrial-political system is more profoundly perverted than he could have imagined. As he becomes more and more entangled in corruption, he starts to resemble the sinister types who once abused him and his family, like Phil Connor. At the same, Jack Duane's undignified exit shows that the Chicago criminal underground will not hesitate to betray its own—everyone is out for themselves, first and foremost.
Over time, Jurgis becomes more and more unscrupulous, and learns the ins and outs of Chicago's criminal underbelly—in particular the corrupt political system. A double-dealing union spy named "Bush" Harper introduces Jurgis to a Democratic boss named Mike Scully. Through Harper and Scully, Jurgis gets involved in a plot to benefit in the long term by rigging an election in the Republicans' favor. Scully's plan is to have Jurgis go to the stockyards and proclaim his support for the Republican party.
Through Jurgis's involvement in the criminal underground, Sinclair can depict the way that underground has come to dominate politics through money, might, and corruption. Notice how the Democrat Scully thinks nothing of working to help a Republican win office if it will make Scully money. Scully has no ideals other than money. For Jurgis's part, he is now so involved in the world of graft that he is willing to deceive even the workingmen who used to be his compatriots to vote against their best interests.
Scully arranges a hog-trimming job for Jurgis. Now, Jurgis earns a salary and also collects illegal kickbacks, and he adopts a more confident air. Jurgis oversees the rapid expansion of the "Doyle Republican Association," and works diligently to ensure that the Republican will prevail. He is so committed that he doesn't think to save some of the graft money for himself, which riles his colleagues; Jurgis soon learns to tap into "the extra bungholes of the campaign barrel."
Even as corruption becomes Jurgis's way of life, he has remained, ironically, honest and hardworking. He's a diligent, loyal criminal. Yet the other criminals actually get angry over his honesty—it interferes with their dishonesty! Over time, he learns to seize every opportunity for his own benefit, regardless of where his loyalties lie: this, the novel suggests, is the capitalist way.
When the election rolls around, Jurgis spearheads voter fraud efforts. The Republican is elected in a landslide, and Jurgis earns hundreds of dollars for himself. He indulges in a tremendous drinking bender while the rest of Packingtown celebrates the election results, sardonically described by the narrator as the "crushing defeat of an arrogant plutocrat by the power of the common people."
The novel's description of this episode of Jurgis's life is bitingly sarcastic. By calling the Republican's victory, which has been engineered by Scully, the "crushing defeat of an arrogant plutocrat by the power of the common people." the narrator illustrates how easily facts can be distorted to hide the basic truth that workingmen are manipulated by the powerful.