Frank Algernon Cowperwood, once a wealthy man despite his youthful indiscretions, begins anew in Chicago after his release from a Pennsylvania prison in the 1870s. Accompanied by his mistress, Aileen Butler, he quickly forges connections with influential businessmen and makes strides to dominate the city's social and economic landscape. However, the challenges he faces are as numerous as his ambitions, testing his resolve at every turn.

Conquering New Territories

Upon settling in Chicago, Cowperwood sets his sights on ventures promising significant returns. His initial triumph is gaining control of the city's gas companies, a feat achieved through his shrewd financial maneuvers. Despite this success, integrating into Chicago's elite social circles proves more difficult. Aileen's vivacious nature and lack of refinement create hurdles in their social ascent. Moreover, past indiscretions from his time in Philadelphia resurface in the press, complicating matters further. Although Cowperwood profits from compelling rival gas companies to buy out his franchises, this victory is tempered by social ostracism from Chicago's power brokers.

Personal and Professional Entanglements

As Cowperwood delves deeper into the street railway business, he acquires control over a horsecar company serving Chicago's northern districts. Amidst this, his wandering eyes settle on Stephanie Platow. Younger and more cultured than Aileen, Stephanie captivates him, filling an emotional void and sparking an affair. Simultaneously, Cowperwood pressures the west side street railway company to cede its franchise to him, but his triumph is bittersweet. He discovers Stephanie's infidelity, mirroring the complex web of his own personal and financial engagements.

Political Battles and Personal Betrayals

The fight for control of Chicago’s city council becomes Cowperwood’s next battlefield. This struggle is compounded by the revelation of Aileen’s unfaithfulness, a personal betrayal that wounds him more profoundly than any business defeat. Despite losing the initial council election, Cowperwood's resilience and ability to exploit his adversaries' weaknesses turn the tide. His shrewd political maneuvering eventually garners the support of even the new mayor, restoring his influence.

A New Romance and New Challenges

Berenice Fleming, a young woman from a questionable background, enters Cowperwood’s life. Enamored, he shepherds her through the high society maze while becoming her lover, despite the considerable age difference. Meanwhile, the race to transition street railways to electric power heats up. Cowperwood faces opposition from rivals eager to claim their share of the burgeoning elevated lines. Undeterred, he makes a bold public gesture, donating a significant sum to a local university to silence doubts about his financial stability.

Relentless Pursuit of Power

With credit restored, Cowperwood is determined to secure his hold over Chicago’s transportation network. However, the realization dawns that he and Aileen will never gain full social acceptance. To cement his legacy, he plans a grand mansion in New York to house his art collection, hoping this will be his entrée into elite circles. In Chicago, he presses forward with elevated rail projects, but his adversaries anticipate his overextension, plotting his downfall.

The Climax of Ambition

The apex of Cowperwood's ambition is to obtain long-term franchises for his transportation empire. However, his control of the Union Loop, a critical piece of the city's transit puzzle, meets fierce opposition. The city's affluent and influential, along with the press, unite against him, deterring even the most daring officials from granting the necessary approvals. Legal barriers also thwart his plans, as his lawyers reveal the state constitution prohibits such extended franchises. Undeterred, Cowperwood hatches a scheme to establish a state transportation commission, hoping it will provide the legal foundation needed for his plans. Though the legislature passes the bill, the governor’s veto crushes his hopes.

Exile and Acceptance

As Cowperwood's personal...