"I see someone who gets up at 6:00 every morning to feed the homeless and still has the time to know the names of every single person in this place; from Oscar at Security to the little old lady in Zoning who likes Twinkies from the vending machine. And I do it not just because I'm a nice person, but because when my boss needs something, I'm the one who gets it done. I killed for this job, lady. I know my rights. I'm not gonna let anyone shut me up."
— Yoli Castillo to Jessica Pearson

Yoli Castillo is Jessica Pearson's personal executive assistant and the former social media coordinator for the city of Chicago's Streets and Sanitation department.


"I'm the voice this place is missing. I'm passionate about the things that are important, and I am not afraid to push on the issues that I care about. Isn't that what we're supposed to do here?"
"Not if it costs us valuable relationships and opportunities."
"I know I can be a lot sometimes, but I'm not stupid. I can learn how to do this job, but you can't teach passion."
―Yoli Castillo and Jessica Pearson[src]

Yoli Castillo is a young woman living in Chicago, Illinois who worked as a waitress before becoming the Social Media Coordinator for the city's Streets and Sanitation department, working for Jeffrey Epstein. One day while talking to Oscar about his daughter while going through security, Yoli met Jessica Pearson. Yoli asks who she is, adding that she knows everyone who works in the building, and is flabbergasted when Jessica reveals she works for Chicago mayor Bobby Novak and can understand and speak Spanish as well. A few hours later, Yoli is notified by a co-worker regarding Novak's public tirade against the media this morning and views the meltdown on Twitter, realizing that it is regarding Jessica. Using her phone, Yoli retweets the viral footage of Novak's run-in with the journalists and posts tweets with hashtags criticizing Novak's administration.

The next morning, Derrick Mayes meets Yoli 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. Yoli returns to City Hall to gather her belongings and encounters Jessica again, whom she blames for the termination of her employment. Jessica convinces Yoli that she played no part in it, while Yoli divulges that she knows everyone in the building, having valued her job, and that she knows her rights and cannot be silenced. Before Yoli leaves, Jessica informs her that there is a difference between knowing her rights and knowing when to use them. Later that night, Jessica has her driver take her to Yoli's house, offering Yoli a job as her assistant, which Yoli accepts.[1]

The next morning, Jessica returns to her office to find Yoli waiting for her with coffee, which Jessica does not like. Jessica asks Yoli to book a lunch reservation for two and to have a dossier ready by lunch regarding information on Betsy Sullivan, whom Yoli explains is a upper-class society woman who holds fundraisers. 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.

Later on that day, as Jessica passes through security at the entrance, Yoli gives Jessica her preferred coffee, having called Donna Paulsen at Zane Specter Litt, and apologizes if she has crossed a line before doing so. Yoli then offers Carlos Salazar, a Latino man who protested for employees being able to speak Spanish at work, as a candidate for alderman. Jessica is not interested in Carlos as she needs a replacement with big, financial backers, although Yoli admits that she thought Jessica would pick Carlos just because he's Latino, believing Jessica to be Latina. Jessica then gets a phone call from Lillian Cook and heads to the Cook residence.

Jessica returns to the office the next day, where Yoli asks about Lillian. Yoli then informs her that she has set a meeting with Carlos Salazar, although Jessica tells her to cancel the meeting, reminding her that it is not her position to push her agenda. Shortly after, Jessica then calls Yoli and asks for information on Cramer. Yoli then asks Derrick for help, as she is unable to gain the information Jessica wants on her own.[2]

The next morning, Yoli attents a meeting with the other City Hall employees, where Derrick and Keri Allen 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.

In her office, Jessica is watching a deposition about Carl Jeffries, a man who was murdered after dropping a lawsuit against McGann and the city of Chicago, when Yoli walks in with a message from Jeff Malone, revealing she spoke in depth about her relationship with Jeff for 45 minutes. Jessica tells her that she needs to work on establishing and respecting boundaries and Yoli asks whether she would call Jeff back before realizing she has overstepped said boundary.

The next day, Derrick is massaging his feat at his work space 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 someone from the Black Panther Party as white people think of anarchist when they hear "Black Panther", although Yoli humorously adds they would think of the Marvel movie. Yoli is about to voice her opinion of them stringing Lloyd along 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.[3]

Sometime later, Yoli is called into Jessica's office to be given an assignment. As Jessica is busy handling a case for Keri, 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.

On the first floor of City Hall, Derrick is waiting for Blake , 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.

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.

Jessica returns to her office that night, 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.[4]


  • Her Twitter handle is @YOLOCastillo.



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