The means two decades of summers full of lying, manipulating, showmances, and unexpected twists have come and gone. With the Big Brother 21 finale on September 25, fans are officially starting to speculate about the winner of the season. But we thought we'd take a trip down memory lane. Congratulations are in order! Their have been 21 (yes 21) winners of BB. Big Brother just named the winner of season 21, and in the end it wasn't much of a surprise.Jackson Michie walked away with the prize, after a … Yes, this show has truly taught us to expect the unexpected. The $500,000 grand prize will either go to Jackson Michie, Nicole Anthony, or Holly Allen. Fun fact: Big Brother officially turned 20 in 2020. Big Brother All-Stars crowned Cody Calafiore the winner of Season 22 with only the second unanimous committee vote in Big Brother history. Big Brother Season 21 came to an end last week, with the jury declaring its winner. In lieu of its usual live studio audience, “Big Brother” wrapped its 20th summer and yet another season of twists, surprises and controversies by awarding its second-ever “All-Stars” winner.