Big Brother: The First 10 Winners Ranked By How Much They Deserved It

Did the first ten winners of the reality TV show Big Brother deserve to win their seasons at all? We’re ranking them by whether or not they earned it!

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While Big Brother has produced some truly memorable winners throughout its history, not all winners are created equal. Some earn the win with their gameplay. Others benefit from a bitter jury. One thing is for sure, some winners are more deserving than others.

The merit of the first ten winners is still debated to this day. Looking back at each winner’s gameplay, here is the ranking of Big Brother’s first ten winners, from least deserving to most deserving.

10 Eddie McGee (Big Brother 1)

Big Brother 1 was a completely different game from subsequent seasons. Instead of having a Head of Household, HouseGuests voted for two people to be nominated for banishment but were not allowed to discuss nominations with one another. Instead of a house vote, a public vote dictated which HouseGuests went home.

This makes it difficult to judge Eddie’s game against other winners. Though popular with viewers, Eddie didn’t have to use any strategy to win the game. While he may have been deserving of winning Big Brother 1, he is the least deserving when compared to the other winners on this list.

9 Adam Jasinski (Big Brother 9)

Due to a writer’s strike, Big Brother 9 premiered in the winter of 2008 instead of its typical summertime slot. Largely panned by critics and fans for the soulmate twist, Big Brother 9 featured one of the show’s least deserving winners in Adam.

His brash personality often clashed with fellow HouseGuests. Early in the season, he made inappropriate comments about individuals with Autism that offended many fans. Adam’s biggest move all season was not getting voted out. Did he win Big Brother? Yes. Did he deserve to win? Not so much.

8 Drew Daniel (Big Brother 5)

At times during Big Brother 5, Drew was viewed as a threat. His 4 Horsemen alliance dominated the game early on, putting Drew in a power position. Nakomis, recognizing an opportunity to take control of the game, proposed the six finger plan which resulted in alliance member Scott being sent out the back door. This took all the power from the 4 Horsemen, turning Drew’s game upside down.

While he did make some strategic alliances with fellow HouseGuests, most notably Diane, that did save him later on, Drew would have been voted out had he not won three out of the last four Head of Households. Nakomis, the HouseGuest who should have won, ended up finishing fourth.

7 Maggie Ausburn (Big Brother 6)

Big Brother 6 is mostly remembered for the war between the Friendship alliance, led by Maggie, and the Sovereign Six alliances. The least popular of the two with fans, the Friendship alliance dominated the game. Maggie had an underrated social game that continually saved her despite being on the block four times throughout the season.

Maggie’s big move though was not making waves within her alliance. Maggie didn’t win Head of Household in the later stages of the game, leaving her alliance to nominate and vote each other out. Due to this, Maggie had fewer enemies on the jury. Janelle, who played with her back against the wall all game, made it to the final three by dominating competitions and was more deserving of the win.

6 Lisa Donahue (Big Brother 3)

Make no mistake, Lisa played a good game. She formed the initial majority alliance and relied on her strong relationships with Eric and Danielle to further herself in the game. She is also the first HouseGuests to ever win the first and last Head of Household competition. While deserving, Lisa, unfortunately, played with a more deserving winner in Danielle.

Danielle used her secret alliance with Jason to dictate almost every vote, controlling the game from the start. Had the jury not returned home and watched Danielle’s diary room sessions, she would have won. Consequently, Big Brother 3 is why jury members are now sequestered.

5 Mike “Boogie” Malin (Big Brother: All-Stars)

Some would argue that Will Kirby should have been awarded a second win during Big Brother: All-Stars, but Mike “Boogie” Malin played an important role in Chill Town’s success. Boogie and Will were the biggest threats entering the house. Despite their reputation for lying and manipulation, they were able to form several alliances, including the Legion of Doom alliance with James and Danielle. They also employed a memorable strategy dubbed operation double date.

After Will was voted out, Boogie won the last of his three Head of Households, voting out Janelle. Boogie dominated the final jury questioning, owning his game while showing Erika rode his coattails to the end. Will is possibly the best player ever, but Boogie was a deserving winner in his own right.

4 Jun Song (Big Brother 4)

The X-Factor twist was largely a dud, but Jun changed the way the game was played by floating in the middle between multiple alliances to earn herself a win. Jun was in the season’s large alliance, the Elite Eight. She was also aligned with ex-boyfriend Jee and the Three Stooges. At the end of the game, she formed the Girl Power alliance with Alison and Erika. Jun was constantly strategizing and wasn’t afraid to shift allegiances if it benefited her game.

Her best move, however, was taking Alison to the end, as Alison was the only HouseGuests more hated then Jun. Jun’s strategy forever changed Big Brother. Floating has become a common strategy used in Big Brother, thanks in part to Jun’s success using the strategy. Future winners, such as Andy Herron, employed similar strategies on their way to victory.

3 Dick Donato (Big Brother 8)

Much like Adam, Dick displayed a brash attitude toward his fellow HouseGuests. Unlike Adam, Dick’s actions always felt like they had a purpose. In a lot of ways, Dick’s strong personality helped propel Dick to the end as someone who was potentially beatable. This also permitted him to be more aggressive with his gameplay, where he was able to vote out his alliance when necessary.

The only knock on Dick’s game is that he should have been voted out in week six but was saved by the America’s Player twist. Still, he used his loud personality and his strong strategic gameplay to further himself and Danielle in the game.

2 Dan Gheesling (Big Brother 10)

Dan is now considered one of the greatest players of all time, but his game was in serious jeopardy early on in Big Brother 10. His initial alliance dissolved once Brian was called out for playing too hard and voted out the first week. Dan, guilty by association, quickly took a step back and focused on building relationships with his fellow HouseGuests while throwing competitions.

Despite being on the outs, Dan was only nominated for eviction twice in the game. He used his strategy to further his game, creating a strong alliance with Memphis, Remy, and Keesha. His strong social game led to some of the best jury management ever seen on the show. Dan’s “mist” is now considered legendary.

1 Will Kirby (Big Brother 2)

The greatest player of all time, Will Kirby earned the victory in Big Brother 2. At the end of the fourth week, Will’s Chill Town alliance member, Boogie, was voted out, leaving Will all alone. Since the Power of Veto had yet to be introduced, Will had to rely on his social game to maneuver throughout the house.

Will received a total of four nominations, yet he continued to find ways to convince the other HouseGuests that he was so disliked that he couldn’t win. This strategy worked well for Will. The jury could see his strategy and influence on Nicole, who he convinced to take him to the end. The jury respected that Will used his status as a threat to trick the other HouseGuests into keeping him. After his Big Brother: All-Stars appearance, Will cemented his status as the best player to ever enter the house.

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