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.

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.

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.

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.

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.

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.

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, 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.

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.