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
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.
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.