In the fifth season, Diane is forced to question whether it’s appropriate for her to help run an African American law firm with Liz when the firm loses two top lawyers. Meanwhile, Marissa and the firm become entangled with Hal Wackner, a regular Chicagoan who decides to open his own courtroom in the back of a copy shop.
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.