Diane Lockhart finds herself living in an alternate reality where Donald Trump was never elected and Hillary Clinton is the current president of the United States. While Diane's liberal self is overjoyed, she soon realizes how a different outcome of the 2016 election might have unexpected consequences.

The office must survive after being trapped by white supremacists.

Mike Kresteva takes his case against Reddick, Boseman & Kolstad to a grand jury, but the firm devises a grand jury strategy of their own to hamper Kresteva's efforts. Colin finds himself in an awkward position in court.

While on his way to court with Maia and a witness, Jay is being arrested by the police. When Diana and Liz rush to help him out, they discover that it is an immigration issue and federal agents are about to deport him. Meanwhile, Adrian goes back to work.

Diane takes on a new client who is accused of cyber-terrorism, resulting in unforeseen repercussions for the firm, especially Lucca. An accident brings Diane and Kurt together. Henry reveals new truths about the scandal to Maia.

Diane and Marissa find themselves arguing at the Circuit 9 3/4 Court, led by the quirky "Judge" Hal Wackner. Meanwhile, Carmen Moyo proves herself to be an effective, yet underestimated, new associate.

At Circuit 9 3/4 court, Marissa is assigned to "prosecute" two contrasting "cancel culture" cases, which both leave her questioning the intentions of Wackner, David Cord and Del Cooper. The tension between Diane and Liz increases while they work together on a high profile case against the Chicago PD.

After a financial scam destroys the reputation of lawyer Maia Rindell, while wiping out her mentor and godmother, Diane Lockhart's, savings, Maia and Diane join one of Chicago's preeminent law firms.

Lucca defends a TV writer-producer in a copyright infringement case with ties to the President of the United States. Meanwhile, Mike Kresteva takes aim at Reddick, Boseman & Kolstad.

A storm is brewing at Reddick, Boseman & Lockhart when revelations of past indiscretions involving a partner come to light. Right when she thought the world couldn't get any crazier, an incident at home pushes Diane to her breaking point. Meanwhile, Lucca is brought a new opportunity while Marissa teaches Maia to toughen up.

Reddick, Boseman & Lockhart are hired to investigate the death of high-profile New York inmate Jeffrey Epstein. Back at the office, STR Laurie continues to tighten their grip on the firm by forcing Diane, Adrian and Liz to conduct layoffs. But the enraged trio won't go down that route without a fight and hatch a plan in hopes of shaking off their corporate overlords once and for all.

Diane raises eyebrows while settling in as a new partner at Reddick, Boseman & Kolstad. Maia continues to deal with the repercussions of her family's Ponzi scheme. Lucca and Maia unexpectedly pick up a new case.

A flashback to 2020 reveals how the team at Reddick, Boseman & Lockhart experienced the year's major events.

Diane is aghast when Kurt reveals he recognized the face of a man featured in a U.S. Capitol insurrection "Most Wanted" poster. Intrigued by Wackner, Marissa sneaks over to his copy shop "courtroom" and is thrilled by what she encounters. Back in legitimate court, Liz uses a current case to tackle Section 230.

Eli Gold's trial is underway, with Marissa Gold as part of his legal team. Liz and Ri'chard attempt to solidify their working relationships leading to a surprise discovery about Ri'chard's history and Liz's father. The firm attends a Democratic fundraiser.

Reddick, Boseman and Lockhart represent an African-American undercover cop, Rashid Clarkson, who was left crippled after being shot by another Chicago police officer in the line of duty. The case's opposing counsel is legend Solomon Waltzer, whose tactics have the firm questioning the legitimacy of his evidence. Diane finds herself at a crossroads with both Kurt and Tully.

When a comedy streaming network executive, Del Cooper, asks Liz to conduct a sensitivity read on one of his comedians, the entire firm ends up fighting over how comedy and 'cancel culture' collide. Meanwhile, FBI agent Madeline Starkey goes after Kurt for his alleged involvement in the U.S. Capitol insurrection.

Ri'Chard's nephew loses his bone marrow donor and it's all hands on deck at Reddick & Associates to save his life. In the midst of the search, Liz discovers Ri’Chard has a hidden agenda.

Adrian and Barbara face a cruel realization about a high profile client. While second chair to Diane on a case, Lucca is in for more than she bargained for thanks to the state's attorney's office’s golden boy, Colin Morrello. Maia visits her father in prison.

Diane and Lucca represent an ovarian cancer survivor looking to obtain custody of her previously donated embryos. Maia is the victim of a fake social media account. Mike Kresteva pays a visit to Reddick, Boseman & Kolstad.

After landing tech mogul Neil Gross as a new client, the firm is tasked with figuring out a way to combat hate speech on his social media platform. Maia's suspicions about her father grow after Uncle Jax pays an unwelcome visit. Lucca and Colin's romance heats up.

A Russian student asks Diane to protect her from deportation, claiming she was one of the women filmed with President Trump in the alleged "Golden Shower" tape. Meanwhile, Maia and Lucca suggest an unconventional lawyer to represent Jay's friend Craig Savador at his upcoming appeal and Colin meets with the Cook County Democratic Committee.

Reddick, Boseman & Lockhart is asked by ChumHum to bring on a specialist, lawyer Brenda DeCarlo (Cheryl Hines), to investigate any remaining misconduct or cultural issues within the firm. Diane begins to question the resistance group's tactics while Blum approaches Maia with an intriguing job offer.

A former divorce client, Duncan Herz, seeks the firm’s help, claiming a buzzy new play running in Chicago is based on his divorce and shares specific details that unearth more than just his dirty laundry. Diane attempts to get to the heart of Memo 618 when a missing case leads her to the corporate overlords themselves, STR Laurie.

Liz and Carmen represent Oscar Rivi, who is suing Harbor Hospital over the wrongful death of his daughter. Jay's investigation of the case triggers some PTSD that forces him to dig deeper into his own experience with Covid. With Madeline Starkey still hell-bent on getting Kurt to come clean, Diane decides to take matters into her own hands.