Source: Courtesy / Courtesy Ashley Hollis approached 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.