"It's our job to do the most good for the greatest number of people."
— Derrick Mayes to Yoli Castillo

Derrick Mayes is the press secretary of Chicago mayor Bobby Novak and a former journalist.


"I'm sorry if I overstepped my bounds. I can get a little overzealous."
"No, overzealous is good in the right hands. It gets things done."
―Derrick Mayes and Jessica Pearson[src]

Derrick Mayes works as the press secretary for Bobby Novak, whom he reveres and idolizes, likening him to Superman. On Jessica Pearson's first day at work, Derrick 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 Allen.

As Jessica leaves Keri's office, she encounters Derrick, who admires her work with the hunger strikers and offers his support. Jessica inquires as to who Derrick is, and he reveals that is Novak's press secretary. Derrick admits that Novak straddles the line on too many issues and that he is glad Jessica is here to push him in the right direction. Jessica tells Derrick that he shouldn't go behind Novak's back only for Derrick to reply that it would be good for Novak. When Jessica states that Novak would not see it that way, Derrick retorts that Jessica did the exact same thing with Alderman Deborah Coates, and that they should fight for the hunger strikers.

Jessica later pays a visit to Derrick, telling him that if he wishes to make a difference and help the hunger strikes, he would give her Alderman Coates' last three tax returns as well as her home address. Derrick asks if it's legal, as he does not wish to do anything illegal, although Jessica merely states that they are putting their money where their mouth is. 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.[1]

The next morning, Derrick discussion re-election with Novak when Jessica arrives, notifying them that the press is in the building. As he is in a good mood, Novak suggests to Derrick that they give the press a statement 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 his workspace in City Hall, he is approached by Jessica, who ask him deliver something to Human Resources on her behalf, as she is unaware where it is. Sensing something amiss in Derrick's demeanor, she presses him for information and he reveals the morning's events with the journalists.

That night, Derrick walks in with four statements Novak could give depending on how the situation played out, and discloses to Novak that a woman in the building 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. The next morning, Derrick meets Yoli Castillo at a bagel truck, informing her that her retweets and hashtags violated the office's social media policy. Yoli attempts to justify her actions by claiming that it was tweeted by her private account as a private citizen, although Derrick replies that she is not a private citizen and that she cannot criticize the administration she is a part of. When she refuses to take the tweets down, Derrick notifies Yoli that she is fired.

After Jessica and Keri manage to get the Chicago PD to renew their contract, Novak then holds a press conference where he announces that the police force is active once again, publicly giving Jessica the credit, with Derrick in attendance. Returning to City Hall, Derrick informs Novak that he is leaving for the night, although not before Novak asks Derrick to have Nick bring the vehicle around.[2]

The next morning, Derrick sees Keri at City Hall, who attempts to go to Novak's office, informing her Novak is not in today, citing personal business, but that he most likely would still attend a scheduled meeting for 2pm. Derrick then asks her to be involved in a PR campaign to make the office look good; despite her initial declination, Derrick convinces the reluctant Keri to participate. Shortly after, Yoli makes her way to the staff kitchen to have a private encounter with Derrick, who is surprised that she is working for Jessica. Derrick apologizes for firing her publicly and offers to give her a private tour, although Yoli asks whether Derrick would have apologized had she not returned to work, taking his silence as an affirmation.

In her office, Keri is photographed by Luke, who is taking photos for the PR shoots. Luke asks Keri out, although she refuses, which Luke construes as her being taken. She then tells him that she is late for a meeting, although as he leaves, Derrick notifies her that the meeting has been cancelled since Novak is spending time with his wife, not noticing that Keri is slightly affected by the explanation. Later, Yoli asks Derrick for help, as she is unable to gain the information Jessica wants on Frank Cramer on her own, and while he chides with her for a while, eventually agrees to help her.[3]

The next day, Derrick and Keri have a meeting with the other employees, where they disclose that Novak has taken the day off work for personal reasons, with Keri being left in charge of the day-to-day. Deputy Mayor Lloyd Triple wishes to take advantage of Novak's absence by pushing forth his agenda to have a street in Chicago named after Fred Hampton, a member of the Black Panther Party, although his attempts are shut down by Jessica. Knowing that Lloyd is firm, Keri approaches Derrick and tells him to team up with Lloyd and claim his plan has been approved, with the intention being to string him along until Novak returns. Derrick is reluctant, not wanting to lie to Lloyd after lying to the press, and Keri reminds him where he works and tells him to find a way to wrestle with his conscience.

Derrick goes to Lloyd's office, notifying him that he had won Keri over. Derrick then notices photos of Lloyd with Bobby Kennedy as well as Lloyd's time serving in the Vietnam War. Lloyd wants Fred to be remembered, upset that Derrick, a black man born and raised in Chicago and attended college in Chicago as well, had no clue who Fred was. Lloyd proposes they discuss the matter with City Council, but as Derrick is tasked to stall him, he notifies Lloyd that they must follow protocol and gain signatures. Lloyd is suspicious, claiming that citing protocol is a tactic to string him along, although Derrick convinces him of his sincerity; in response, Lloyd informs Derrick that the pair would go out canvassing the neighborhood for signatures.

The next day, Lloyd and Derrick are in the neighborhood collecting signatures. Derrick asks why commemorating Fred Hampton is so important to him, and Lloyd divulges that he and Fred were childhood friends, and that Fred was merely fighting government oppression and police brutality when the FBI raided his house and shot him, putting two more bullets in his head when the first one did not kill him. He adds that he had spoken with Fred the day he had died, wanting to hang out together, although Fred refused, claiming that it would not be safe for Lloyd to be seen with him.

Derrick returns to City Hall, massaging his feat when Yoli comes up to him. Yoli is proud that Lloyd's plan of naming a street after Fred Hampton is coming to fruition, only for Derrick to reveal that they're just stringing him along. Derrick claims they cannot name a street after Fred due to him being a Black Panther, citing that white people think of anarchist when they hear the name. Yoli is about to voice her opinion when she holds herself back, stating that she has a problem respecting boundaries and therefore will keep silent, only for Derrick to reply that she should not let anyone silence her. With permission to speak freely, Yoli berates Derrick for his actions and tells him to pick a side.

Inspired by Yoli's words, Derrick heads to Keri's office, informing her that they got 612 signatures in one day, allowing them to petition City Council. Keri attempts to thank Derrick for his participation in her ploy, only for Derrick to accuse her of not wanting to Fred commemorated as she comes from a police family, while hiding behind the veil of wanting to protect Novak. Derrick tells her that she should at least give Lloyd some respect before leaving the signatures on her desk and walking out.[4]

A short while later, Derrick waits on the entrance floor of City Hall for Blake Everett, one of the vice presidents of Ickaris' Corporate Affairs, 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.

Yoli and Derrick give Blake 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.

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, 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. Derrick then manages to convince Blake and gets the deal signed.[5]



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