As the founder of Level Six, Winston wasted no time trying to surround himself with strong players. While he successfully laid low during the first week, his paranoia became very apparent when he was used as a pawn by Kaitlyn Herman against Swaggy C. Though he survived eviction the second week, he and Brett Robinson became targets by HOH Scottie Salton because of their strong bond. Seen as a liability, his former alliance and their affiliates decided to vote him out over Brett, sending him home in a 6-5 vote; he came in 14th place.
Age: 28 Hometown: Somerset, KY Current city: Bowling Green, KY Occupation: Medical sales rep Three adjectives that describe you: Active, ambitious, and passionate. Favorite activities: Hiking, long walks or driving with my dog, working out, and watching movies. What do you think will be the most difficult part about living inside the Big Brother house?
I've been living alone for two years now so isolation is somewhat normal for me, but that feeling of total cutoff from friends and family will be a struggle. Which past Big Brother cast member did you like most? Paul Abrahamian. His mix of gaining other's trust while simultaneously screwing with them was iconic. Do you have a strategy for winning the game?
Yes, I hope to use my interpersonal skills to gain trust from key individuals identified early. But unlike Cody Nickson from last year, you cannot come in and split the house too early. It's a waiting game. My life's motto is...
Give your all today, for what you keep, you lose forever. What would you take into the house and why?
My dog. Duh.
My record player with some music because I have to have music.
Fun facts about yourself:
I write love notes to my dog before work.
I volunteered for Big Brothers and Big Sisters in 2016 and 2017.
I hold my high-school record for the 40-yard dash for over a decade.
I've been mistaken for Justin Timberlake and Ryan Reynolds.
The four also flew out to Fiji to do pre-season press for Love Island.
Winston would go on to fly back out to Fiji to participate in Love Island as a contestant. He entered the villa on Day 9, first appearing at the end of Episode 7. He never officially coupled up with anyone, and after being left Single at the third Recoupling Ceremony and fifth overall elimination, he was dumped from the island and left the villa on Day 15, in Episode 13.