Ashley Hollis navigated through unexpected twists, betrayals, and multiple evictions to become Big Brother Season 27 winner. The Chicago native outwitted 17 contestants to take the crown with an overwhelming 6-1 vote, relegating Vince Panaro to the runner-up position. Winning the popular reality competition show, Hollis has set herself up for a showbiz career while securing a life-changing prize of $750,000.
An underdog throughout the season, Ashley Hollis didn’t win Head of Household until the last day, and it made all the difference. She’s determined to make the best of her prize money. “I am very good with my money,” she told Entertainment Weekly after winning the competition. “So I’m definitely not going to spend it. I’m going to live within my means… [but] I’ll definitely give a good chunk of my money to my parents, just because they’ve given everything to me my entire life.” Despite her newfound fame, much is yet to be learned about the Big Brother winner. But here are facts every Ashley Hollis fan should know.
1. Ashley Hollis Is A Lawyer
@cbsmornings Ashley Hollis outlasted twists, backstabbing and evictions to be crowned the winner of the @CBS reality show @Big Brother. She revealed she kept her career as an attorney a secret, playing up a different persona, an act that helped her manipulate allies and secure the win: “I really got into my method acting.” #bigbrother #reality #cbs #ashleyhollis
The Big Brother winner is a Georgetown Law alumnus. She attended Loyola Marymount University’s College of Business Administration, where she obtained a Bachelor of Business Administration. She graduated magna cum laude, majoring in marketing with a concentration in business law. Ashley Hollis later acquired a Juris Doctor from Georgetown Law.
In July 2025, she was sworn into the New York Bar. This saw her obtain an attorney license from the New York State Bar Association. Going into the Big Brother house, Hollis kept her profession a secret as part of her game plan. She believed other contestants would see her as a threat if they knew she was an attorney. So she played dumb, manipulating fellow HouseGuests to secure the win.
2. She Now Wants To Pursue A Career In Entertainment
https://www.tiktok.com/@ashleyhollis_/video/6843212836466920709
Winning Big Brother Season 27 has been a life-changing experience for Ashley Hollis, who has now relegated her law career to the background. She has decided to pursue a career in the entertainment industry. Hollis disclosed this on her LinkedIn page, divulging that the decision to leave her “Big Law job” for the Big Brother house transformed her personally and professionally.
“While law will always be part of my foundation,” she wrote, “I’ve decided to take a step back from the legal world (for now) to explore new opportunities in entertainment. I’m currently in talks with several management companies about representation as I look to monetize and grow my digital platforms, pursue on-camera hosting opportunities, and continue building my presence in television and media.”
3. Ashley Hollis Has Always Been Drawn To Show Business
Getting the opportunity to pursue an entertainment career is a dream come true for the Chicago native, who has always been drawn to the industry. As a child, she longed for a showbiz career, engaging herself in whatever endeavor she imagined would help her entry into the industry. From acting to competitive dancing and modeling, Ashley Hollis did it all!
In 2023, she competed in the Miss DC pageant, securing a top-five position to win a $3,000 consolation prize. Even as a lawyer, her career leaned towards the entertainment industry. She worked with Fullscreen, Sony Music Entertainment, and Paramount Pictures in Los Angeles before joining Shearman & Sterling LLP at their New York office in May 2023.
4. She’s Open To Returning For An All-Winners Season
https://www.tiktok.com/@ashleyhollis_/video/7556064132202581303
Ashley Hollis quit her job to compete in Big Brother Season 27. It has been a worthwhile experience for the lawyer, so much so that she’s willing to embark on a second outing for an all-winners season. “I’ve seen the circulation of an all-winners season. I would definitely do something like that,” she told The Wrap. “Hopefully I’ll get a better edit, because I’ve been hearing from the fans that the edit of me was not accurate. So I would love to do it again…,” added Hollis.
5. Ashley Hollis Is A Childhood Friend Of Big Brother 23 HouseGuest Hannah Chaddha
One of Big Brother Season 23 HouseGuests, Hannah Chaddha stood out for being the first Indian-American contestant. The Season 23 alum and Ashley Hollis have been friends since they were kids. When the lawyer emerged as the winner, Chaddha celebrated her on Instagram, declaring their friendship. “My oldest friend just won Big Brother. Congratulations Ashley Diane Hollis, from daycare till now, forever my winner pick,” she wrote. Check out 5 things you didn’t know about the Clarkson’s Farm star, Harriet Cowan.
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