Ashley Hollis is many things: a Georgetown Law graduate, a former attorney at Skadden specializing in mergers and acquisitions, a certified yoga instructor and the reigning champion of Big Brother Season 27. The Chicago native made history on CBS by becoming the third Black female winner in the show’s history, taking home $750,000 after outsmarting 15 competitors over 90 days of strategic gameplay. Now she’s transitioning from the courtroom to the spotlight, pursuing acting, hosting and music while using her legal expertise to comment on culture and entertainment. In this conversation, Hollis breaks down how she applied courtroom tactics to reality television, her thoughts on diversity initiatives and what comes next in her rapidly expanding career.
You were nominated in the very first week yet still won it all. At what point did you realize you could actually take this thing?
I would say week six, when Riley went home. Riley was a very controversial houseguest and a strong competitor. When he left, I realized I was not on anybody’s radar anymore. I went from the biggest threat in week one to pulling strings behind the scenes. I was a big reason why Riley even went up in the first place. I worked hard that week to make it happen, and when he got evicted, that whole side of the house crumbled while my side rose. That was when it hit me that I could really win this game because I was being underestimated, which was my strategy all along.
In your final speech, you talked about strategically downplaying your brilliance. As a lawyer, how hard was it not to lead with that dominance?
It was very difficult, especially because there were men in the house who would talk down to me. They thought I was flamboyant and didn’t pick up on the fact that I was acting. I was embodying Elle Woods from Legally Blonde, and it really played into my favor. People would tell me information or accidentally spill things they thought I wouldn’t pick up on. But as an attorney, we’re very analytical. We pick up on every single detail, no matter how small. We’re also very forward-thinking, which allowed me to always have a step ahead on my houseguests because I was thinking of different paths to get to the end.
Was there ever a moment in the house when your legal instincts directly saved your game?
Yes. A really pivotal moment was week 10 when Will went home. I was on the block next to Will, the most likable guy in the house. He’s 50-plus, has swag and charisma. Everybody liked and respected him, and I was sitting next to him thinking, how can I pivot? My lawyer skills helped me build counterarguments against him. I realized I needed to make people see that his likability was bad for their game because if they sat next to him in the final, they would lose that $750,000. Even though he was injured and couldn’t compete, I argued that they needed an ally who could win competitions and take them off the block. That’s what you do as an attorney. You look at what makes the other party weaker and figure out how to get a jury on your side.
Aside from the money, why did you want to do a national TV show like this?
I loved the experience, but let me be honest, I also love the money from being an attorney. In all seriousness, it took a lot to get through law school and then pass the bar. A lot of people don’t realize the bar passage rate is very low. It’s not just Kim Kardashian who fails. Sometimes half or more than half of people don’t pass. I really wanted a new opportunity and pivot. I’ve always been passionate about entertainment, television, hosting and speaking. There are so many different facets to me, and I just turned 26. I wanted a new life experience, and I always have my degree. My parents always said a degree is something nobody can take away from you. You can always go back to it as your foundation. A lot of people dive right into entertainment, and it doesn’t work out, and they have no plan B. I got my educational goal first, and I can always fall back on it.
Watching the season back now, what move are you most proud of, and what would you undo if you could?
I would undo changing my vote in week four. I said I evict Kelly when I meant to evict Jimmy, then I went back to change my vote. Apparently that had never been done before, and I broke the internet. I was trending on Twitter, which I found out after. It was truly a mistake. We’re sleep-deprived in that house, sometimes getting four hours of sleep with bright Hollywood camera lights filming everything. People thought it was funny, so I guess it’s fine, but I would take that back. My proudest moment watching back is how I clocked everything. People online were asking if I had a genie in a bottle because I was identifying every alliance and situation without even having confirmation. I owe that to my lawyer skills. We’re able to sniff out everything, and I have a very good read on people.
How has winning Big Brother changed how people take you seriously in rooms you now enter as a media personality?
People actually take me more seriously now, which is surprising. We’re in a time where social media and TV are dominating Hollywood and entertainment. You’re seeing influencers in movies and getting Grammy nominations. My final speech, which went viral, helped people take me seriously because they saw me switch up and display my intelligence. Having both facets now, the entertainment side and a Georgetown law degree, actually helps. I didn’t embarrass myself on TV. I stayed true to myself the whole process, so I don’t have anything to be embarrassed about or not proud of.
Let’s talk about some legal topics. Jason Derulo recently had a sexual harassment case dismissed. What does dismissed really mean for public perception versus courtroom reality?
Dismissed typically means the judge could not find enough facts to support a case going further, or someone didn’t submit documents on time. Usually, the core facts weren’t there to even build a case or reach any conclusion. It could also mean somebody missed a deadline. It varies depending on what court filing and what state, and whether that person could even refile again.
Wendy and Eddie Osefo are facing charges related to credit card fraud. What are some common misunderstandings people have about these types of financial crimes?
The key thing about federal cases is once they file, they already have their case built. Federal courts never indict someone without already having the facts. That’s why you typically see in federal cases people get time. Once the feds come for you, they already got you most of the time. They’ve been building for months before they even file. I think we’re going to see her and her husband do some time. It’s very rare that the feds don’t win their case in some aspect. From what I read, they have photos to prove their case, and there were filings with different insurance companies. Even if someone has a defense, when the feds come, they typically already have everything they need.
Pharrell recently fired back at DEI criticism. What legal pressures are companies actually feeling around DEI, and what’s performative versus policy-driven?
Personally, I think DEI is amazing. I can speak from experience because Georgetown was under heat from the Trump administration, as was my law firm, for supporting certain nonprofits. People get confused and think DEI means putting people in rooms they’re not supposed to be in. That’s not what it is. DEI is about giving already qualified people who meet the standards the opportunity to be in rooms they already qualify for. Georgetown and Harvard are two of the most diverse law schools, but Black students are still less than eight percent of the population. Everybody I know who went to Georgetown had the same statistics as everybody else, if not more. I don’t really care if it’s performative or not. If we’re getting people in rooms they’re supposed to be in and giving them platforms to succeed, that’s what matters. CBS put a diversity program in place around 2020, and the first Black winner happened that season. I’m the third Black female winner now. Whether corporations are doing it for the right reasons or not, we’re seeing results. People of color are being put in amazing positions. Our stories matter just as much.
Darius McCrary’s recent release from jail reignited conversations about celebrity and the justice system. What’s something the public consistently gets wrong about these situations?
This is similar to what happened with the Central Park Five, where many were pressured to admit guilt when they were actually innocent. We see this is a huge problem, specifically in the Black community, of not having correct legal representation to understand the terms you’re accepting. There’s also the corruptness of the legal structure and pressure from prosecutors to have convictions on their record. This is a huge inequity because people don’t have the right representation. Court-appointed attorneys typically aren’t the best because they have so many cases and are overworked. They don’t have enough time to give cases what they need. People accept things they don’t understand. They’re told if you accept this plea, you’ll get three years, but if you go to trial, you could get 30. When you accept a conviction, it’s on your record. It really boils down to getting the right legal representation and supporting nonprofits that help place people with strong attorneys.
With this massive new platform and credibility in multiple industries, what kind of empire are you building next?
I definitely want to get into hosting, whether interviewing people or doing red carpets. I love to talk, as you can tell. I’ve always been passionate about that. I used to want to be a broadcast journalist, but law felt like the guaranteed path. Now I see so many attorneys are broadcast journalists on TV doing corresponding work. I’m also pursuing acting. I started an acting class and I’m getting headshots this weekend. I also sing and I’m currently working on a song. I’m looking forward to getting into everything and building my social media. All of the above.
Where to find Ashley Hollis:
Fans can follow Ashley Hollis on Instagram at @ashleyhollis_, where all her platforms are linked in her bio. She’s also active on TikTok and Twitter under the same handle, @ashleyhollis_. For those interested in her music covers and lifestyle content, she recently launched a YouTube channel under the username Ashley_Hollis. All updates about her acting career, hosting opportunities and new projects can be found across her social media