Bobby Novak is the mayor of Chicago and the half-brother of Nick D'Amato.
Bobby Novak is the mayor of Chicago and the half-brother of Nick D'Amato, as well as the lover of Keri Allen. Shortly after Jessica Pearson moved to Chicago, she exacted a $4 million settlement from his office on a police brutality case. After representing Lillian Cook to prevent Novak and property developer Pat McGann from tearing down public housing to construct buildings, Novak had Nick and Keri handle Harvey Specter and Jessica respectively. While McGann managed to have Harvey's ability to practice law in Chicago suspended, Jessica managed to have an incriminating photo taken of him, forcing McGann to contact Novak. Novak then had Nick pick Jessica up in his car and drive to a secluded location where they could finally meet, where Novak informed her that McGann's building was going up regardless but that he would offer her the chance to work alongside him if she dropped the case, which she agreed to do. However, Jeff Malone informed Jessica that the Justice Department was considering Novak as a suspect to the original plaintiff in the public housing case who had recently been murdered.
A few days later, Nick picks up Novak outside of his house. Novak mentions that his wife Stephanie told Nick to come inside, although Nick claims he likes the fresh air. As Novak prepares to enter the car, Nick tells him not to get involved with "the Pearson woman." However, Bobby tells him that he hired her due to the way she handled McGann.
At City Hall, Derrick Mayes has a conversation with Novak about upgrading the ports, although Novak decides to tell the longshoremen they would upgrade the ports without actually doing it in order to buy them time, much to Derrick's dismay. Derrick also informs Novak that the press is aware Novak's buses have been late again and are asking him for a statement, as Novak had promised that the buses would be fully electric by the end of the previous year and that nearly half of the old fleet is broken down or off the road. Novak tells Derrick to just write a statement on his behalf that doesn't make him look stupid before dismissing him, asking to have a minute alone with Keri. As they step inside the office, Novak asks Keri about the buses, and she replies that a man named Dennis Nivens is obstructing them as Novak did not give him the Lansing contract. Keri then assures Novak that she would handle the matter as she handles everything else for him, although Novak suggests that Jessica would be a better fit, as she ran a huge New York firm, has skills, free time and wants to be back in the field. Keri wonders how Jessica would be able to work for Novak if she has a lawsuit against the city, only for Novak to tell her that there is no longer a lawsuit. Keri is against it, mentioning that she was the one who had Jessica's license to practice law in Chicago removed and that Jessica had accused her of sleeping with him, although Novak merely replies that she should stay in her lane while Jessica stays in hers.
When Jessica arrives at City Hall, Novak presents her with her own office. Novak tells her that she is late, to which she responds that it was because she was at a school that he was shutting down, only to have Novak respond that City Council is shutting down Franklin due to budgetary concerns. Jessica reveals that she has discovered that the alderman is Deborah Coates, whose allegiance Novak needs as Coats has very wealthy financial donors. Novak replies that Coates is an ally and a friend, and tells Jessica to instead handle the electric buses issues, stating that the lack of buses affects more people than whether Franklin High School remains open. As he leaves, he welcomes Jessica to City Hall, asking her not to be late again.
Novak then heads to a bowling alley to meet Pat McGann. He hands McGann the lawsuit, telling him he could rip it up, although McGann realizes the deal Novak made, adding that he hoped Novak made better ones during his time as a public defender, claiming that he had just given away the store. McGann berates Novak for bringing Jessica into City Hall, although Novak claims that if he hadn't, Jessica would have dug into McGann's finances and discovered that his dirty money came from the mayor's office. McGann adds that Jessica could find out more stuff about the two of them, only for Novak to claim that is why he hired Jessica and that he is merely keeping his enemies close.
Back at the mayor's office, Novak berates Jessica for ignoring her electric bus assignment and alienating Coates, one his closest allies. He explains that he wishes he could keep every public school open but that he has to make choices, and informs Jessica that if she can't do that, he'd be willing to sever ties with her instantly. The next day, Keri heads to Novak's office, complaining about Jessica's actions. Novak gives his support for Jessica, saying that he is glad Jessica is actually listening to the assignment he had given. Keri demands to know why he had hired Jessica, and he replies that there is a lot of dirty stuff he has to do and that it made Keri sick to kick out the people of the North Park neighborhood into the street just so McGann could construct a building, and that he values Keri too much to have her involved in the dirty side of things. He then approaches her, stroking her hair while admitting that it has been weeks since they've been together and that he misses her. However, Keri states that she has worked too hard to be seen as the girl who has slept her way to her position, and that since Jessica views her as such, she is reminded of that every time she sees Jessica. She then walks out of Novak's office, claiming it is ironic that Jessica is the reason they can no longer sleep together.
As Nick drives Novak back home, he notifies his brother that he met up with McGann earlier in the day. Novak insults McGann, claiming that McGann is trying to divide them, although Nick replies that he needs an ally and asks where he would be if the truth were to ever come out. Novak replies that he has looked out for Nick ever since he found out they were brothers and that Nick, as a cop, has received the detail every other cop in the city wants because they are family, adding that Nick is the one who chooses not to enter Novak's family home. As Nick remains silent, Novak informs his brother that he loves him before walking into his house.
At the City Council meeting, Coates rescinds her support for the dismantling of Franklin High School and announces her resignation as Alderman of the 54th Ward, much to the joy of those in attendance. Derrick reveals to Novak he was aware of this and gives Novak a statement to read. Returning back to Jessica's office, Novak mentions how Jessica went behind his back, and how Coates is now Vice President at Midwest Portage, the bus company. Jessica explains how Coates would make sure the buses went into production on time, thereby solving both the hunger strike and the electric bus issues, making Novak look good in the public eye. Novak reveals that he was the youngest alderman ever elected, at the age of 26, after having served for one year as a public defender. He explains that in his first month, he had tried to raise minimum wage to $7.25, admitting that it was half of what the minimum wage should be. After succeeding in his endeavor, he was warned by the oldest alderman what would happen if he bit off too much too soon. He adds that while Jessica is a smart woman, her antics affect his name and not hers, to which Jessica replies that this is new to her and that it would take her a little time to acclimate to the fact that she isn't the one calling the shots. She also adds that she believes Novak doesn't want her taking smaller bites, but that he had hired her as he needs problems solved. She asks him what McGann has on her, only for Novak to smile and tell her that she should paint the office walls blue before leaving.
Novak pays Keri a visit at her apartment, claiming to be worried about her as she had left work early. Keri states that she is not Novak's girl and that she is not sticking around to fight out whether Jessica would be replacing her or not, prompting Novak to reply that he doesn't care about who has power in the office, adding that Keri is the woman he needs. As Keri begins to say that his wife is the one he needs, he kisses her, and she responds by kissing her back. The pair then begin to take each other's clothes off as they continue kissing, while outside her apartment, Nick waits for Novak in the vehicle.
The next day, Novak is discussing re-election with Derrick in his office when Jessica walks in, apologizing for being late. As he is in a good mood, he offers her the day off as he is in a good mood. On his way out the door, Jessica warns him that the building is full of press who wish to exact a statement from him. Novak and Derrick prepare to do so, although Novak becomes angered when one of the journalists inquires as to why he hired Jessica and demanding to know whether what Jessica does for him is legal, prompting Novak to storm out. In his vehicle, Novak lashes out at Derrick, as Derrick used to be a journalist himself. Derrick replies that he was bound to be asked this question at some point, only for Novak to point out that Jessica hasn't even worked 48 hours yet and that she isn't on payroll, and therefore the media should not know she works for him. Novak then orders Derrick to do his job and to find every question he would ever get asked about the matter as well as a respective answer.
Returning to City Hall a few hours later, Novak encounters Jessica. Novak refers to her as a liability, informing her that the police deal came apartment due to Jessica's targeting of the 13th Precinct. Jessica justifies her actions by stating that they brutalized a man in handcuffs, though Novak says it was just two bad cops whereas Jessica made the entire department look bad and therefore the police despise her, and that without the contract being signed, Chicago would no longer have an active police force. Jessica replies that he should have had an answer this morning to the question of why she was hired but they could now show the press why and suggests taking down McBride, the underpaid union lawyer who went after Novak in the first place; Novak merely replies that it is Keri's case and therefore Jessica must take it up with her.
Returning to his office, he meets Keri, who notifies him that the fire department will double their demands once they discover what the police department turned down. Novak wonders if this is Eric McBride merely posturing as he is a lawyer and not a police officer, although Keri explains that he is practically one of them as he has been their union lawyer for 14 years; additionally, Keri adds that as someone with a police family, she understands the resentment towards Jessica. This prompts Novak to ask whether it was Keri who leaked Jessica's employment to the press, although Keri denies the accusation and voices her discontent that Novak would entertain the notion that she would ever harm him.
Novak goes to a pub to talk to police superintendent Chuck Hargrove. Chuck refuses to have the police sign the contract since Novak hired Jessica, who tarnished the entire department, and asks Novak why he would hire her. Novak replies that he has his reasons and that Chuck should trust him, reminding him that he had taken money out of Public Health to give the police a fair deal, to which Chuck replies that while he knows that, the rest of the police force does not. Chuck also reveals that since the other officers they believe he is too friendly with the Mayor, he had to cut ties with him to avoid losing them, and adds that so long as Jessica was part of Novak's administration, the city would not have an active police force.
Back in his office, Novak has a phone call with his wife, Stephanie, notifying her that he would not be able to come home as he is busy. She reminds him that he had promised their son that he would have gotten home before he went to bed, although Novak merely tells his wife that he would make it up to him some other time. As he ends the call, Derrick walks in with four statements Novak could give depending on how the situation played out, and discloses to Novak that Yoli Castillo has been retweeting the viral footage of Novak's run-in with the journalists with unflattering hashtags; Novak tells Derrick to do his job and handle the situation. As Derrick leaves, Novak turns on the television to a news broadcast.
Nick goes to Novak's office to bring him lunch, and mentions having driven Jessica around the other day, as well as Jessica's request be her driver. Novak refuses, reminding Nick that his job is to drive him only, only for Nick to ask whether staying outside Jessica's apartment all night was part of the job, adding that the last time he was stayed outside all night waiting for someone was for Novak's father. Later that night, Novak finds out that the police contract has been renewed; he goes to talk to KEri and realizes it was Jessica's doing, while Keri suggests that he could use the situation to justify Jessica's employment. Novak then holds a press conference where he announces that the police force is active once again, publicly giving Jessica the credit. Jessica then takes the stand and addresses the audience, informing them that her father was from Chicago and that she wishes to give back to the city, and allows the reporters there to ask her questions.
Back at City Hall, Novak goes to see Jessica in her office, where he reveals that he became aware that she leaked her own name and employment to the press. Jessica explains that she had done so because she knew it would eventually get out and that she wanted to be in front of it, while Novak states that she merely wanted the firestorm so that she could receive the credit for quelling it. He adds that she put his career in a dangerous position before returning to his office, where he sees Keri and Derrick. Keri suggests they go out for drinks, but Novak tells Derrick to have Nick bring the vehicle around while notifying Keri that he wants to go home so he could put his kids to bed.