In Big Brother 8, Dick, along with Dustin Erikstrup and Jessica Hughbanks, was part of the "Rivals" twist. Dick's rival was Daniele Donato, his estranged daughter. Dick was known for his various personal attacks on houseguests as a means of intimidation after he and Daniele were nominated during Week Six. He narrowly escaped eviction in week 6 due to America's Player which required America's player Eric Stein to vote to evict Dustin Erikstrup instead of Dick despite Eric wanting to evict the latter. Both he and Daniele made it to the Final Two, where he won the season in a 5 to 2 vote.
He returned for BB13 where he was partnered with Daniele, and he formed the Veterans Alliance. However, he left the game in the first week due to an emergency; Donato later revealed he left the game after learning he was HIV-positive from a blood test given to him by the producers. He placed 14th.
Dick along with his daughter Daniele Donato originally made it into the casting process for Big Brother 6 where the duo was among 40 potential houseguests but they were not chosen to be one of the Final 14 houseguests for the start of the season.
Dick's actions in BB8 has made him arguably the biggest and most notorious villain as well as one of the most memorable houseguests in Big Brother history. He has been referenced several times following his performance in BB8, and many future players have tried to copy some aspects of his game.
Donato hosts an online Big Brother recap show called "Dick at Night", which features alumni, various celebrities, and evicted houseguests.
Donato, alongside his girlfriend Stephanie Rogness-Fischer, appeared on an episode of the fifth season of the VH1 reality show Couples Therapy, which aired on September 10, 2014.
On October 1, 2014, Donato revealed that he has been HIV-positive since 2011, first learning that he had the virus after given a blood test by the producers during Big Brother 13. Donato says that this is the reason why he walked away from the house that season.
Coincidentally, all three players won by a 5-2 vote.
He is the first and only winner to not participate in the first HOH and have immunity the first week.
Dick is the oldest finalist and the oldest winner by date of birth on Big Brother US. Dick is also the oldest finalist in a standard season of Big Brother (US), being 44 while competing. Dick was the oldest finalist overall in both categories until Marissa Jaret Winokur won Celebrity Big Brother 1 (US) at the age of 45.
Dick is the only returning player to walk from the competition.
Dick is the first person to survive eviction week 2 and become HOH week three. He would later be followed by Matt Hoffman, Helen Kim, and Alex Ow.
Nicole Franzel and Scottie Salton also were nominated week 2 and became HOH week 3, however, Scottie was vetoed off the block and Nicole won the Battle of the Block and was dethroned as HOH in week 3.
On the live feeds of Season 8, Dick revealed that his son agreed to send him a coded letter from home should he win HOH (Which he did week 3). The first letters of the first and last paragraphs were the initials of the houseguest he should least trust. If the letter said his son and his girlfriend were doing well, Dick could trust the people he was working with. If the letter said his son had broken up with his girlfriend, he could not.
As a result of this, in all future seasons production rewrites the letters before giving them to the houseguests.