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.
- "You can't publicly criticize the administration when you're a part of it."
"Okay, well, I don't happen to share that opinion, but sorry, I guess?"
"You need to take it down. Now."
"Wait, I just apologized to you when I didn't really mean it, that's a lot for me. I start buckling to censorship, I'm on the slippery slope to hell."
- ―Derrick Mayes and Yoli Castillo
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.
- Her Twitter handle is @YOLOCastillo.