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.

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.

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.

An unfortunate event brings the firm together, along with the prospect of a new name partner. Diane struggles to grapple with the insanity of the world, and Maia is confronted with another hurdle in her parents' scandal.

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.

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.

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.

Un flashback al 2020 rivela come il team di Reddick, Boseman e Lockhart ha vissuto i principali eventi dell'anno.

Nel finale della quinta stagione ci sono troppe corti e troppo poco tempo per la gente di Reddick/Lockhart. Marissa sta preparando una forte difesa alla corte di Vinetta per Matteo, mentre Diane tenta di ottenere un'intervista con lui per far uscire Matteo dalla corte. Carmen, Liz e Allegra difendono lo spacciatore Oscar Rivi mentre i pubblici ministeri tentano di rimetterlo in prigione.

Dopo essere stata promossa a socio anziano dell'azienda, Liz è costretta ad accettare Ri'Chard Lane come nuovo partner nominato per aiutare a gestire il suo personale e il carico di clienti. Nel frattempo, Diane sperimenta un déjà vu mentre si fa strada nel suo nuovo ufficio, al piano di sotto con gli associati.

L'ufficio deve sopravvivere dopo essere stato intrappolato dai suprematisti bianchi.