Bobby and Keri’s past comes back to haunt them when the former city attorney hits the Chicago with a lawsuit that requires Jessica’s help to sweep it under the rug, while Derrick and Yoli toe the line between doing their jobs and doing what’s right.
In a flashback from five years ago, Alderman Bobby Novak attempts to charm Deputy City Attorney Keri Allen, recognizing her as one of the attorneys who defeated US Steel. Keri is not interested in Novak as he is married, despite Novak stating that he and his wife have separated. After a conversation in the elevator, Keri tells Novak that he cannot always rely on his handsome looks, reminding him to do his job and serve the people who elected him.
In the present day, Keri is at her apartment while a shirtless Luke is eating in her kitchen. Noticing his presence, she informs him that she does not wish to be rude but that he must leave. Luke jokingly refers to her actions as "love 'em and leave 'em", and on his way out, asks Keri out on a date. Seeing the look on Keri's face, he backpedals and claims he was kidding, but asks if he could still call her, which she agrees to. Moments after, she receives a knock on her front door, only for it to be a process server delivering a lawsuit.
Jessica Pearson walks into Novak's office, where Nick D'Amato is sitting. She questions Nick as to why he did not drive her to work that morning, to which he apologizes and claims that Novak needed his coffee and doughnut first thing back. Novak tells Jessica to handle digging into longer-term projects for him. Noting that the files Novak is handing her are for technology and manufacturing, she realizes that he wishes to have Chicago house Ickaris' second headquarters, and asks him if he really wants a headache at the moment. Novak mentions that the headache would be worth it as it would bring half a billion dollars in construction, to which Jessica reveals that she knows the truth regarding Novak's absence and thus reiterates whether he wants this particular headache. Novak looks at Nick to see whether Nick had told her, and he indicates that he did not. Jessica then claims that she understands what he is going through and offers herself as someone he can talk to, although he dismisses her and tells her to start on the project.
Jessica returns to her office, where Keri is waiting for her. Keri discloses that the city is being sued by Ken Sharma, the former city attorney. Jessica replies that it is Keri's job to defend the city from lawsuits, but Keri clarifies that she does not wish to fight the lawsuit in court but merely wants for it to disappear, citing that making things go away is Jessica's specialty. Jessica tells her that if she wants the case dropped, it would either mean she does not want something getting out or she is afraid of the outcome, although Keri responds that Novak is listed on the lawsuit as well and that she wishes to protect him.
After Keri leaves, Jessica calls Yoli Castillo into her office to give her an assignment. As she is busy handling the Keri assignment, she tasks Yoli with giving Blake Everett, one of the vice presidents of Ickaris' Corporate Affairs, a tour through Chicago in order to convince him to choose the city as the base of their new headquarters. Yoli is uncharacteristically reluctant, prompting Jessica to ask why since Yoli's desire was to be directly involved in city affairs, to which Yoli explains that she is not a fan of Icakris, asking Jessica why she can't do it. However, as Jessica claims she is busy, Yoli decides to put her personal opinions aside and accepts the job.
In another flashback from five years ago, Deputy City Attorney Keri takes over a case for the previous attorney, Ricculi, who has gone on maternity leave. Keri offers a $7,000 settlement from the city to Gabrielle Aquino, the mother of a young man who illegally ran between train cars and got crippled as a result. However, Gabrielle's lawyer states that the city's responsibility to maintain the trains supersedes her client's son's violation. Keri explains that while that is true, the Safety and Inspections department would prove in court that the trains were maintained, which would lead to them getting nothing. Gabrielle responds that she asked for the safety inspection reports and never received them, and when Keri is confused, her lawyer adds that her office requested them three times as per legal disclosure discovery but did not receive them, much to Keri's surprise. Keri then returns to City Hall to see city attorney Ken Sharma, explaining that she tried to find the reports on her own but could not. Sharma responds that he would handle the matter himself, adding that if the Safety and Inspections department don't hand something over, the attorneys then figure out they don't need it, leaving Keri with a suspicious look on her face.
In the present, Jessica goes to see Sharma, stating that Sharma is lucky to still be a member of the State Bar after cheating clients out of liability claims for years, and that he is only suing for the city for wrongful termination because he is out of money after going through a divorce and because his career hadn't recovered after leaving City Hall. Sharma responds that the suit isn't about what he did, but about when Keri did, adding that she knows what she did, while his attorney Ben Dunbar retorts that their deposition would be on Wednesday.
On the first floor of City Hall, Derrick Mayes is waiting for Blake Everett, as he had been tasked by Novak to give him a private tour of the city, only to realize that Yoli was given the same task herself. He states that the two have been chosen as they are millennials, though Keri is still reluctant as they would be whitewashing the city during the tour while paying no mind to the gentrification. Momentarily, both of their phones begin to vibrate and they head out the door to begin the tour, with Yoli jokingly mentioning that Derrick always wanted to be a tour guide.
Jessica returns to Keri's office and notifies her that she is being deposed. Keri is frustrated, as she had wanted Jessica to get the case dropped and is now forced to bring in outside counsel, although Jessica claims that she can still get it dropped. Jessica suggests that she prepare Keri for the deposition, adding that she had been through many of them before and that Keri had trusted her instincts to come to her before and therefore should trust her again, adding that whatever Keri does not want coming out would definitely come out otherwise.
Flashing back again to five years ago, Keri goes to see Alderman Novak at the Polish restaurant he had mentioned earlier. She alleges that Sharma is mishandling evidence, stating that she went through his previous cases where the settlements were much less than expected and that evidence was missing. However, Novak reminds her that whistleblowers are rarely rewarded and that if she came forward, she would be forced out of City Hall. Sometime later, Novak goes to see Pat McGann at one of his buildings, still in construction. There, McGann tells him that he is now a prime candidate for Mayor as the previous contender, Assistant District Attorney Mills, had been caught having a sexual affair with a paralegal. Novak admits that while he agreed to play the long game and do McGann's bidding on City Council, he is sick of the city's reputation and that as it is getting to him, he wants to be a new kind of mayor. Despite his statement, McGann scoffs at him, citing that he has many rich people supporting Novak and that Novak won't be any kind of mayor if he doesn't win, with McGann even having paid $20,000 to have a consulting firm appraise Novak's strengths and weaknesses.
Yoli and Derrick give Blake Everett a tour of the city, although Yoli criticizes and insults him for spending a fortune on a new corporate building while his company's workers rely on food stamps. While Blake had heard such criticisms before, it had not been from a member of an administration attempting to court him, and leaves. Derrick then admonishes Yoli for her actions, with Yoli protesting that it was Derrick who had told her before to speak her mind and not get silenced, adding that Derrick disagreed with Ickaris' actions as well. Derrick then states that his personal opinion does not affect his job, which is to help the mayor, and that securing the Ickaris contract would have assured the employment of 4,000 Chicago citizens.
That night, Keri goes to see Novak in his office, where he is clearly upset. Keri inquires into Stephanie Novak's well-being and realizes that Novak is upset that she told Jessica, although Keri justifies her decision by claiming that Jessica cannot work so closely with him and not know. Novak then lashes out, stating that he spent thousands of dollars, two days, and a battery of tests for the doctors and the scans to have no results, and that all he wants is answers, claiming that in five years, he would be out of office and that Stephanie would be in a wheelchair. Following the end of his tirade, Keri leaves Novak to his own devices.
As Jessica prepares to go home, she sees Nick waiting outside the mayor's office and asks him how come he hadn't left yet, with Nick replying that he clocks out when Jessica does. Nick is still irritated at Jessica's suspicion of him for the murder of Carl Jeffries, despite Jessica's assertion that he is cleared of any doubt in her mind, as Nick is upset that she believed he could do such a thing. As Jessica tells Nick to lower his walls and let him in, he points out that she has not done the same, and asks her what she meant by her earlier statement to Novak when she claimed she understood what he was going through, also adding that she may as well be someone programmed to write checks and issue sound bites. Jessica then retorts that Nick doesn't know anything about her, to which Nick replies that therein lies the problem; he does not know anything.
Blake gives Derrick a tour at one of the company's factories, where Blake reveals that he is soon flying to Atlanta to meet its mayor, adding that 18 other cities are vying to make a deal with Ickaris. Derrick, who had apologized on Yoli's behalf, attempts to sway Blake to pick Chicago by claiming that others are saying the same thing as Yoli and that, if he picks them, Novak's grassroots organizations, a corporate accountability team, would partner with them where both sides would benefit as a result. Blake replies that he believes Chicago would benefit more, but states that if the city were willing to give tax cuts on every community concession, he would reconsider. Derrick then asks whether Ickaris would issue a public statement that Chicago is one of their top three choices in return for getting Novak to sign off on the tax cuts, and Blake gives his word.
Back at City Hall, Jessica deposes Keri privately, asking Keri about Sharma. Keri discloses that Sharma was her mentor who hired her straight out of law school, with Sharma as City Attorney and Keri as Deputy City Attorney. However, after nearly two years, Keri discovered Sharma was mishandling evidence, which led to Sharma's departure from City Hall and Keri succeeding him. Jessica asks why Novak's name is on the lawsuit, as Novak was alderman at that time and not mayor, to which Keri divulges that it was Novak who ousted Sharma. Jessica follows up by asking how long she had known Novak, and when Keri responds that it was only a week, Jessica poses the question of why Keri would trust someone she barely knew for a week and risk her career in the process; Keri claims that she was doing what she felt was right, only for Jessica to claim her actions led to Novak making her the youngest city attorney in the history of Chicago; when Keri protests, Jessica further suggests Keri exchanged sexual favors in exchange for professional advancement, causing Keri to storm out.
In another flashback, Keri goes to Alderman Novak's office to inform him that she cannot hold the information back and that she is going to come forward. Novak tells her to take a moment to consider her actions, believing momentarily that she came to see him to get him to talk her out of it, but when she states that she is sure of what she wants to do, it leads to the both of them heading to Keri's apartment to have sex. The next morning, Novak tells Keri that he would be ousting Sharma in her stead, taking the risk on her behalf as a show of thanks. Keri initially believes that he is referring to the sex, sardonically stating that he may as well leave cash on the dresser, although he clarifies that he wishes to thank her for reminding her why he went into politics to begin with. He tells her that while he loves being an alderman, he is lazy, complacent and numb, but that due to Keri, he feels lively again, and that he needs to do this for her.
Jessica goes to Keri's apartment to discuss the case, where Keri orders Jessica to pay Sharma whatever he demands. Jessica attempts to tell Keri not to give in to Sharma's demands, although Keri replies that if the issue gets out, the public would find out that not only did Keri sleep with Novak at that time, but still does, adding that while Novak would recover, the rules are different for women and that she would always have a reputation of a woman who slept her way to the top.
Back at City Hall, Yoli presents Derrick with a newspaper that talks about Ickaris considering Chicago. Yoli asks Derrick how he got Novak to sign off on the tax cuts, to which Derrick responds that Novak did not, upset at his actions since his job is to help the mayor, not go behind Novak's back and authorize deals on his behalf. Yoli replies that Derrick could have simply told Novak he was cleaning her mess, and when Derrick responds that he doesn't throw people under the bus, Yoli retorts that he could have because she is not ashamed of her beliefs. This prompts Derrick to ask Yoli why she works for the government despite having zero respect for how it works, to which Yoli states that the government does not work for everyone. Derrick states that working for everyone is not only impractical but impossible, and that their job is to do the most good for the greatest number of people. Yoli believes Derrick has sold his soul, although Derrick replies that he believes in a lot of the same things Yoli does, but that he is also a lot smarter in getting them done. Yoli quips back that despite his assertion, they are both standing in the same place right now despite her staying true to herself, and Derrick asks her not to take him down with her the next time she stays true to herself.
That night, Jessica meets Sharma at a pub. Sharma believes Jessica is coming to cut a deal after Jessica admits the jury might find a man who lost his job due to the machinations of an ambitious city attorney and an equally ambitious alderman sympathetic, but that he wouldn't win. Sharma explains that he gave $10,000,000 to public schools rather than use it to pay someone who skipped school to jump between train cars, calling it a fair deal. Understanding that Sharma wants revenge on Novak and Keri, Jessica offers him $1,000,000, which he refuses. Before he leaves the bar, he tells Jessica that he gave 20 years of his life to the city, and that despite serving two decades, he is nothing to the city anymore. Jessica then calls Harvey Specter and asks him for a favor. While Harvey initially decides to fly to Chicago, Jessica tells him that he can do this particular favor from the comfort of New York, and he asks her what the favor is.
In another flashback, Novak heads to his office to find McGann waiting for him. Novak gushes about the exhilaration of exposing Sharma during City Council and claims that he is now ready to run for mayor, believing his actions have garnered him public support. However, McGann calls him an idiot, notifying him that the big money backers who were prepared to fund his campaign all pulled out as they were friends with Sharma. Novak attempts to tell McGann that he doesn't need his help and that he can rely on public support, although McGann reveals that he isn't trying to have Novak become mayor out of the goodness of his own heart. McGann reveals that Novak's father had Tommy Diehl, a corrupt union boss, killed in exchange for McGann having Novak installed as mayor; McGann then adds that if this knowledge were to be made public, the people would not support him for mayor. McGann then hands Novak a drink, toasting to his upcoming campaign, but informs Novak that he would have to get rid of Keri. The next day, Novak goes to see Keri, who explains that Sharma's absence has given her a lot of work to do and that people believe her affiliation with a married alderman is the reason why. Keri states that she doesn't want to be the reason Novak doesn't get back with his wife, although Novak notifies her that he is considering running for mayor and that he would bring her with him if he wins.
Back in the present day, Jessica heads to Keri's office to tell her that the problem has been solved without the city paying a dime. She explains that all Sharma wanted was for his name to mean something again, but that since it wasn't going to happen in Chicago, she called Harvey to arrange for Sharma to have a corporate job in New York City, informing Keri that she still has powerful friends there. Jessica then apologizes to Keri for jumping to conclusions and accusations on how she got her job, adding that the truth is that Novak got his job because of her and that she wishes the world knew it. Jessica then returns to her office, asking Yoli how the matter with Blake went. When Yoli replies that it concluded smoothly, Jessica asks how much ass-kissing Derrick had to do to clean up her mess, revealing that she was aware of Yoli's actions. Jessica threatens to fire Yoli, adding that she is almost never wrong about a person but believes she was wrong about Yoli, although Yoli responds that Jessica is wrong about being wrong about her, claiming that she has passion and is not afraid to push on topics she cares about; additionally, she states that while she can learn do her job, passion cannot be taught and asks for a second chance, which Jessica grants.
Luke stops by Keri's office to ask whether he had left his watch at her apartment. Keri tells him that she hadn't seen it but that she would look for it, but when Luke tries to kiss her, she rebuffs him, telling him that she is in a relationship with someone else and therefore cannot continue her relationship with him.
Jessica goes outside City Hall to see Nick waiting by the vehicle, and as she approaches him, she divulges that the reason she told Novak she could understand what he was going through was because her ex-husband, Quentin Sainz, had ALS, and that despite all her power, she was powerless to help him fight against his affliction. Nick asks her why she didn't tell Novak, and she replies that the story ended with Quentin dying, which she felt Novak wasn't ready to hear that yet; additionally, she tells Nick that she couldn't truly understand what Novak was going through because Quentin was diagnosed after they divorced and that she didn't know how she would have handled it if they were still married. An emotional Jessica tells Nick that she doesn't know why she is telling him this, although Nick commends her for it, stating that she is a better person than she thinks she is.
Suddenly, a car approaches. As Jessica and Nick watch, the car stops at the curb and its driver gets out, revealing himself to be none other than Jeff Malone. Jessica tells Nick that she won't need a ride home from him tonight and goes to Jeff, kissing him. Jeff tells her that he flew down from Miami to see her, and as Jessica enters the car, Jeff looks at Nick, with the two exchanging glances.
- Gina Torres as Jessica Pearson
- Bethany Joy Lenz as Keri Allen
- Simon Kassianides as Nick D'Amato
- Eli Goree as Derrick Mayes
- Isabel Arraiza as Yoli Castillo
- Gabriel Macht as Harvey Specter
- Mat Devine as Luke
- Amol Shah as Ken Sharma
- Stephen Friedrich as Blake Everett
- D.B. Woodside as Jeff Malone
- Ann Hu as Robin Chen
- Susan Ortiz as Gabrielle Aquino
- Chip Sickler as Process Server
- Joel Spence as Ben Dunbar
- Ken Sharma, the former city attorney, sues the city, Keri Allen and Bobby Novak for wrongful termination. Years ago, during her tenure as Deputy City Attorney, Keri had discovered that Sharma was mishandling evidence and lining his own pockets while cheating victims out of claims, and had reported his indiscretions to then alderman Novak, who ousted him in front of city council. As all Sharma wants is to be respected again, Jessica calls Harvey Specter for a favor and has him give Sharma a new opportunity in New York City in exchange for dropping the suit.
- Goddamn Counter: 0
- According to an official synopsis for the episode, Yoli and Derrick are tasked with giving a CEO the Chicago tour. However, in the episode itself, Jessica clarifies that Blake Everett is not the CEO but rather one of the vice presidents of Corporate Affairs.
- Keri states that she was Deputy City Attorney in 2013 and that after a little over a year, she became City Attorney in 2015 after Ken Sharma's departure. As the events of Sharma's departure is explicitly stated to have occurred five years ago, this would place the episode and the series in 2020. Not only is this inaccurate, with the episode itself releasing in 2019, but as the Pearson episodes takes place a day or days after the previous episode, starting from the Suits episode "Good-Bye", which served as this show's backdoor pilot, the show is currently taking place in 2016, meaning that a "five years ago" event would have been in 2011.
- When Jessica calls Harvey, the computer in the background reveals that the firm is called Zane Specter Litt Wheeler Williams. However, the firm at the time this episode canonically takes place in should be called Zane Specter Litt, as Samantha Wheeler and Alex Williams would not have been promoted yet.
Process Server: Are you Keri Allen?
Process Server: This is for you.
Novak: Pat, listen to me. I know we've been talking about this for a long time and I agreed to play the long game and do your bidding on city council but the more I'm inside, the more this shit gets to me. I wanna make a mark.
McGann: You are good! Well, you save that for the campaign–
Novak: I'm not fucking around. This city's got a reputation for a reason, and I'm sick of it. If I'm gonna do this thing, I want to be a new kind of mayor.
Derrick: Fucking kidding me? You can't talk to that guy like that.
Yoli: You told me to speak my mind.
Yoli: Yeah, the other day. And weren't you speaking yours before this asshole showed up?
Derrick: That was my personal opinion. I don't make policy decisions. My job is to help the mayor.
Yoli: The mayor lets them build IckarisWorld here, you're gonna have a lot of angry voters.
Derrick: He'll have 4,000 people thanking him for a job. That's what he's gonna have. Or was. Fuck!
Keri: I'm the city attorney. I can make a nuisance suit go away by paying it off. [...] Pay him.
Jessica: The man cheated people out of millions and lined his own pockets, unless you are lying and you just made it up to get his job.
Keri: Fuck you.
Jessica: That's not an answer.
Keri: I didn't. You know I didn't.
Jessica: And that's what the jury will hear.
Keri: The jury's gonna hear a woman who was sleeping with the soon-to-be mayor and still is. There, I said it for you. Hope you're happy. If this gets out, Bobby will be crushed, but he'll recover. And me? No matter what anybody says, I will always be the woman who slept her way to the top. It's different for women, and you know that. I will never recover.
Harvey: Don't tell me, the mayor fired you and you're coming back to New York.
Harvey: You took over and you renamed the city Pearson.
Jessica: That's more like it.
Novak: You should have seen the look on Sharma's face when I exposed his corrupt ass to the city council. It was beautiful. Now I'm ready to run. What's the matter, Pat? City attorney a friend of yours?
McGann: No. No, your your big money backers were friends with him, and now they've all pulled out.
Novak: Fuck 'em.
McGann: "Fuck 'em?"
Jessica: You didn't cut all my ties when you took a knife to my career. I still have powerful friends in New York. I made a call.
Keri: To who? What's gonna happen to him?
Jessica: They're lawyers, Keri, not mobsters. Harvey Specter is connecting him with some corporate firms in the market for a Michael Clayton.