On Big Brother 2 (US), Will was known for his friendship with fellow housemate Mike "Boogie" Malin, his showmance with Shannon Dragoo, and getting nominated four times and staying in the game with the help of his over the top clever strategies. On Day 82, he won $500,000 that season after staying 82 days inside the house and receiving the majority of votes from the previously evicted houseguests.
On Big Brother All-Stars (US), Will entered the house with a huge target on his back due to being the only winner in the game. However, with the help of fellow Big Brother 2 housemate and "Chilltown" member Mike "Boogie", Will was able to manipulate other houseguests (most notably his new showmance parter Janelle Pierzina) and managed to get rid of big names like Howie Gordon, James Rhine, and Danielle Reyes just to name a few. Will's ultimate demise was during the final 4 when Erika Landin and Janelle caught onto Chilltown's schemes. Since Mike "Boogie" was the HOH of that week and could not be evicted, Janelle, the Power of Veto holder of that week, casted the sole vote to evict Will from the house, making him the 6th member of the jury. At the finale, Will voted for his ally Mike "Boogie" to win the game.
Will competed on the Big Brother Primetime Special of The Price is Right that aired on May 24, 2016.[2] At the end of the episode, it was revealed that Will was declared the winner.[3] He donated his winnings of $51,030 to charity.
Trivia
Dr. Will created the term "Showmance" which is now widely used in reality programing.
Despite being recognized as the best Big Brother player in history, Dr. Will has never won a single competition. This is cited as part of his strategy as he has stated that Big Brother is based on psychological strategy and not winning "meaningless" competitions.
Dr. Will saved Ophelia, the pot belly pig, from drowning in the BB2 pool.
CBS released the results of the contestants IQ score but retracted them when Will threatened legal action. Before the retraction it was reported that his IQ was 130.
Survivor contestant Rob Cesternino claims he based his game on Will's.
