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.

Reddick, Boseman & Lockhart attempt to adjust to their new landscape as a small subsidiary of STR Laurie, a huge multi-national law firm. Diane encounters a familiar face in court, Louis Canning, during an eminent domain case against a large real estate developer, Rare Orchard. Lucca is given an exciting, high-profile divorce case, however it comes with an unexpected partner, David Lee.

When DNC head Frank Landau asks Reddick, Boseman & Lockhart for help with a plan to engage African-American voters, the resulting discussion turns personal for one of the partners. Determined to sue Rare Orchard, Diane is shocked to learn that all court documents associated with the case are missing, leading her down an unexpected rabbit hole. Meanwhile, Marissa befriends Caleb Garlin, an STR Laurie associate.

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.

Following their secret rendezvous, Liz and Caleb find themselves on a case together, defending a soldier court-martialed for sabotaging the weapon of his superior officer. Lucca accompanies her client, and newly minted friend, Bianca, on a short but sure to be memorable trip to the Caribbean.

Reddick, Boseman & Lockhart represent an Olympic hopeful who was edged out of a spot on the U.S. women's swim team due to a last minute change to the eligibility window. From racism to sex and gender constructs, the case quickly takes the firm into rough waters. Meanwhile, Adrian is approached by the DNC with a compelling offer and Diane and Julius unite to track down Memo 618.

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.

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

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.

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.

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.

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.

When Reddick/Lockhart associates start posting anonymous hate messages about Julius and Diane on a new interoffice app, Diane's name partner position at the firm is once again questioned. At home, Diane grapples with her marriage after learning Kurt is considering a job offer from the NRA. Meanwhile, Wackner goes to real court to have his approach and sanity questioned.

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.

Julius fights to defend himself in Wackner's court in a surreal and harrowing effort to reclaim his car...and his dignity-all because of an alleged parking violation. Meanwhile, after focus group feedback threatens to sink Del Cooper's reality show about Wackner, both Marissa and Wackner embrace different tactics to help revive the court

Liz and Diane struggle to get David Lee and the Dubai overlords to accept the new name partner, Allegra Jurado. Oscar Rivi attempts to make his cannabis business legitimate, but realizes that the corporate world can be just as cut-throat as his own. When the justice system fails to detain and prevent a man from continually committing anti-Asian hate crime, the cops discover another way for justice -- Wackner's court.

In the season five finale, it's too many courts and too little time for the folks at Reddick/Lockhart. Marissa is mounting a strong defense in Vinetta's court for Matteo, while Diane attempts to get an interview with him in order to spring Matteo from court. Carmen, Liz, and Allegra defend drug dealer, Oscar Rivi, as prosecutors attempt to put him back in prison.

After being promoted to top partner at the firm, Liz is forced to accept Ri'Chard Lane as a new name partner brought on to help manage her staff and client load. Meanwhile, Diane experiences déjà vu as she navigates her way in her new bullpen office, downstairs with the associates.

As Diane encounters her first "therapy" session, she begins to see everything in a positive light. After agreeing to participate in a student project about Black female attorneys, Liz must find a way to prevent an unfair takedown of her reputation. Eli Gold returns to help Marissa in court.

Ri'Chard and Liz team up to work on a case about racial discrimination between a Black coach and an NFL team owner. Ben-Baruch returns and stirs up friction with Carmen.

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.

Ri'Chard, Diane and Elsbeth Tascioni are hired to negotiate a "push-nup" for a husband and wife trying to determine fair compensation for childbirth. However, a challenge is presented when the unborn fetus also gains representation in court. Marissa gets a gun after her near death experience with her father and grows wary of strangers around her.

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.

The firm learns major funds are being held by the government due to Russian sanctions, which ultimately leads to a discovery of the FBI’s interest in the firm. Parents sue a college for tuition refunds, raising the question “Who is responsible for the ongoing racial discord in this country?”

While STR Laurie is investigated by the FBI, Liz and Ri'Chard attempt to take their clients. As they fight to extricate themselves from STR Laurie, Ri’chard and Liz must decide who is head of the firm. Meanwhile, Diane is forced to expose her PT-108 treatment.

Diane, Liz and Ri'Chard strategize with Neil Gross to help him buy out the Democratic Party. Jay brings Carmen into the Collective to help extract information from a white supremacist. Diane and Kurt battle relationship issues.

The office must survive after being trapped by white supremacists.