Adrian becomes an overnight celebrity after his candid appearance on a cable news show goes viral. Lucca, who has yet to formally announce her pregnancy, worries about her future at the firm. Adrian’s newfound cable news fame grabs the attention of Chicago’s top law firm and the jury of his latest case.
A Democratic National Committee consultant approaches Reddick, Boseman, and Lockhart to develop a confidential impeachment strategy for the DNC against President Trump, leaving the firm's partners at odds. After an impromptu visit from Colin's mom, Lucca is left feeling suspicious of her motives. Maia is intrigued by Ruth's assistant, Carine.
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.
Reddick, Boseman and Lockhart is left in disarray after a partner at the firm becomes the latest “Kill All Lawyers” victim by an unknown assailant. The Chicago police chief causes a stir when he goes after the firm’s high profile clients Lemond Bishop and Colin Sweeney as potential suspects. Amidst the chaos, Colin is reminded of his true feelings for Lucca.
Heated debates occur at the firm when Liz and Maia represent a well-known photographer, Ron Williams, suing a woman who provided an account of their relationship to a website. Jay continues to investigate possible suspects in Adrian’s shooting while Diane receives surprising news from her accountant.
The FBI question Diane as part of a job background check on Kurt, leading to unexpected and serious consequences. The mayor of Chicago invites Adrian and Julius to join a 'think tank' tasked with figuring out how to spend funds that will address the "Kill All Lawyers" problem. Chaos ensues in the delivery room after Lucca goes into labor early.
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.
Corruption incarnate enters the courtroom in the form of attorney Roland Blum, Maia's new co-counsel on a murder trial. The firm interviews a potential new head of matrimonial law, but Lucca is skeptical of his qualifications. Diane lets off some steam after finding out who recommended Kurt for a new job.
Diane is encouraged to "do something" after meeting the leader of a female resistance group whose aim is to sink POTUS approval rating. Maia and Blum's plan for a plea deal goes awry when Assistant State's Attorney Spencer Zschau takes over the case. Lucca receives a surprising new divorce referral while Marissa helps Julius find a campaign manager to support his run for federal judgeship.
Lucca's involvement in a viral "mothering while black" video sparks conversations at Reddick, Boseman & Lockhart that unearth racial biases and pay disparity at the firm. Liz joins Diane at a resistance group meeting but their next act -- to help swing votes in key states -- hits close to home when the group decides they need a celebrity influencer. Maia faces serious consequences at the firm thanks to Blum.
Blum weasels his way to a co-counsel seat on Reddick, Boseman & Lockhart's largest case against genetics testing company Second Helix. While volunteering as democratic poll watchers in the suburbs of Chicago, Lucca and Jay come face to face with an alt-right group aiming to intimidate voters. Meanwhile, Maia attempts to move on while the partners grapple with a divided firm following revelations of pay disparity.
Celebrity hairdresser Wade V seeks Lucca’s help with a postnuptial agreement for a high profile client. Following their deal with Second Helix, Blum makes his presence well known at Reddick, Boseman & Lockhart, rattling some partners more than others. With political pundits buzzing about the resistance group's covert efforts, Diane takes her axe throwing to the next level.
Diane and Liz deal with a close ally when assigned to a class action case involving malfunctioning voting machines in the 2016 presidential election. Blum's domineering tactics continue to push buttons at the firm while he purposefully stalls his work on Second Helix. Lucca is intrigued by a handsome associate of Blum's.
Felix Staples rattles the firm when he returns with a case against ChumHum, bringing along a familiar face as his representation, Solomon Waltzer. Diane receives a mysterious note at home, leading Kurt to question what she's been up to. Actor Gary Carr shadows Lucca for his upcoming role as a lawyer.
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.
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.
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.
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.