The Big Brother champion and Georgetown Law grad weighs in on DEI debates, federal cases and justice system inequities
Ashley Hollis isn’t just a reality TV champion. The Georgetown Law graduate and Big Brother Season 27 winner brings a unique perspective to today’s most pressing legal and cultural issues. After winning $750,000 by outsmarting 15 competitors on national television, Hollis is using her platform to break down complex legal topics affecting the Black community and beyond. The former Skadden attorney combines her legal expertise with her newfound media influence to offer commentary on everything from dismissed harassment cases to diversity initiatives under fire. In this conversation, she tackles the legal headlines everyone is talking about with the same strategic thinking that made her a champion.
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, whether guilty or not guilty. There wasn’t enough information to even move forward. 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. So it really depends on the specific circumstances.
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. You saw Diddy get time. Jen from Salt Lake City got time. Once the feds come for you, they already got you most of the time. They’ve been building for months and months before they even file. That’s why sometimes people think they get away with things, but these cases take a long time to build. Jen got indicted and then nothing happened for two years because they were building their case. Unfortunately, when the feds come for you, they already have everything they need. I think we’re going to see her and her husband do some time unless they can absolutely prove without a doubt this didn’t happen, which they’re typically not going to file without already having facts. From what I read, they have photos to prove their case. They have photos of her wearing jewelry after filing claims that it was stolen. There were also filings with different insurance companies. When the feds have a case like this, it’s very hard. The record shows feds win their cases in most aspects. You may get off with less time, but I think we’re going to see them do some time.
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 really under heat from the Trump administration, as was my law firm and about 20 other firms, for supporting and funding certain immigration nonprofits. People get very confused about DEI. They think it means putting people in rooms they’re not supposed to be in. That’s not what it is. DEI is about already having qualified people who already meet those standards and giving them the opportunity to be in rooms they already qualify for. That’s just the reality. Georgetown obviously has a huge diversity program, but the Black population is still less than eight percent. Georgetown and Harvard are two of the most diverse law schools in the nation, and the percentage still isn’t that high. Everybody I know who went to Georgetown had all of the same statistics as everybody else, if not more. It’s really about giving these people an opportunity. For me personally, 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 and excel, that’s the more critical and important matter than whether it’s performative. I’m sure some of it is performative, but at the end of the day, if we’re getting results from these actions, that’s all that matters. CBS put a diversity program in place around 2020 or 2021, and the first Black winner happened that season. I’m the third Black female winner now. Whether these corporations are doing it for the right reasons or not, we’re seeing results. People of color are being put in amazing positions because of these policies. Less than two percent of attorneys are Black. Let’s put these people in rooms they already should be in. Yes, some companies might be performative, but let’s also give grace and praise for companies who are doing it because they actually want to. We are seeing results in the Black community. Mara Brock Akil has her deal with Netflix. Tyler Perry has his deal with Netflix. These shows are doing numbers. People want to see Black culture and Black people succeed in entertainment, so whether it’s because of a DEI initiative or not, 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 when it comes to deals. There’s also the corruptness of the legal structure and pressure from federal prosecutors and regular prosecutors to have convictions on their record. This is a huge issue and inequity because people don’t have the right representation. Legal representation and having good legal representation is so important. Unfortunately, just having a court-appointed attorney typically isn’t the best because they don’t necessarily have your best interests, and even if they did, they have so many cases. These appointed attorneys are overworked. They don’t have enough time to give cases what they need. You see people accepting things they don’t even understand the terms of. Sometimes they’re told if you accept this plea, you’ll get three years, but if you go to trial, you could get 30. They take these deals thinking they’re good, but what they don’t realize is 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 amazing, strong attorneys who can do their cases justice.
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. 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 legal commentary, entertainment career and new projects can be found across her social media platforms.