Ashley Hollisapproached Big Brother the same way she approached her legal career: prepared, pragmatic, and unafraid to make a calculated leap. The Season 25 winner, who entered the CBS competition while being an active entertainment attorney and became the third Black woman to win the show, told BOSSIP that the decision to trade courtrooms for confessionals was intentional and rooted in discipline and advice from two pivotal people.
“My parents always told me one thing,” said Hollis. “You can go do whatever you want to do, but a degree is something that nobody can take away from you.”
With her law degree secured and professional credentials firmly in place, Hollis saw the moment as an opening instead of a gamble.
“Now, obviously, I have this platform on TV and plan to just hit the ground running. I love being able to mesh all my passions in one when I can.”
Hollis also shared that despite feeling ready for the moment, she nearly passed on Big Brother altogether.
“I thought I could get a leave of absence so I could just go back to work if nothing works out. They told me no. The maximum was 10 days,” she recalled, referencing the sequester period. “I prayed on it, and something just pulled inside of me and told me, like, this is for you. You got it. You gotta go for this.”
Once inside the house, Hollis’s calm confidence raised eyebrows, and as the viewers saw, it resulted in several attempts to oust her.
“They tried to get me out multiple times because I was just chilling,” Hollis told BOSSIP. “What they didn’t realize is I always came in with a strategy, and I carried out that strategy from beginning to end. They underestimated me. And they found out, honey. They did.”
Her legal training played a major role in her gameplay, and the attorney used it to her advantage.
“Being a lawyer allows you to be a forward thinker,” Hollis explained. “You are always thinking ahead, anticipating what the other side could argue, and figuring out how to minimize their strong suits while making yourself stronger.”
Ultimately, her final speech was like that of a supercharged courtroom closing argument, one that sealed her win.
Outside the Big Brother house, Hollis is putting her legal savvy to use, breaking down pop culture court cases. On the defamation dispute involving Milagro Cooper and Megan Thee Stallion, she offered a reminder for journalists and bloggers alike.
“Always allegedly, allegedly is key,” she told BOSSIP. “Because what you cannot do is give your opinion as if it is fact.”
She also weighed in on the federal fraud allegations surrounding Wendy and Eddie Osefo of Real Housewives of Potomac.
“She is facing 16 counts, including fraud, conspiracy, and false statements to a police officer,” Hollis said. “When the feds come for you, they typically already have everything they need. If the photo evidence is true, that shows intent, and that element is met in the case.”
Source: Matei Horvath/GA / Getty
Hollis stressed that entertainers must be vigilant when signing contracts.
“You need a good attorney reviewing those deals. A lot of contracts have mandatory arbitration clauses, which means you cannot even file in court if something goes wrong. That arbitrator may be affiliated with the corporation. If you cannot control that, it is a huge issue.”
Now firmly cemented as a reality TV champion, Hollis is wasting no time parlaying her win into a broader push across entertainment while racking up digital views and impressions across her YouTube (@Ashley_Hollis) and @Ashley101 Snapchat.
“I am working on a single, I am acting, and I just got my headshots back,” said the multifaceted standout.
From closing arguments to confessional rooms, Hollis’ next act is already taking shape, and we’ll continue to tune in.
