Hollis made history as the Big Brother season 27 winner for a few reasons. Plus, Ashley is the first black woman to win Big Brother while sitting next to a white man. Ashley Won On Her Social GameAshley Hollis during the Big Brother season 27 finale. On the live feeds, cast members like Ava Pearl often complained about how competition-focused Big Brother season 27 was turning out. Had Big Brother 27 been less of a competition-based game, Ashley may not have won against a player that made multiple bold moves.