Big Brother 15 just wrapped up and I thought this was the perfect time to revisit this Big Brother Winners post. There’s nothing worse than investing your summer watching this show, only to witness some loser win it all in the end. Meanwhile all your favorites sit in the jury house waiting for finale night… or worse, at home. Through the years, there are have been some deserving winners and on the flip side, some equally atrocious ones. Sit back and see if you agree with my assessments.

Since Big Brother 1 was solely based on public nominations, votes and evictions, I’m not going to include that season in my rankings. That season was a complete bore because of two words “CHICKEN GEORGE“. If you don’t know what that means, be thankful you don’t. That individual and his rabid fans are why that season went down the sh*tter.

Check out my list below, starting from BEST WINNER to WORST WINNER. If you don’t agree with any of my placings, I’d love to hear about it in the comments. Keep in mind, everyone has their personal favorites. I’m prefacing this by saying I’ve never been a Dan Gheesling fan. I just don’t get the love. Bring on the hate all you Dan fans.

Season 2

Winner: 14. Will Kirby (left)
Should’ve Won: Will Kirby (right)

This is one of the few times in Big Brother history that the person who deserved to win, actually won. Even though this was the second season of Big Brother, it was completely a brand new game. The show received a major overhaul, completely eliminating the public out of the equation. Producers wisely realized the American public was voting out all the entertaining characters and keeping the nice SLASH boring ones in. Like Richard Hatch is to “Survivor”, Dr. Will is to Big Brother. He’s the godfather of this game. When his alliance was dwindled down to just him, he managed to escape eviction every week til the end. The feat was even more impressive, considering there was no “Power of Veto“, “Coup D’Etat” or any other special powers back then. It was just HOH and a social game. He was evil, manipulative and charming all wrapped up in an attractive package. In my eyes, he will forever be… the “Best Big Brother Winner Ever“.

Season 4

Winner: 13. Jun Song (left)
Should’ve Won: Jun Song or Alison Irwin(right)

With three seasons under their belt, the BB producers mixed it up with the format this year. For the first time ever, some houseguests had an existing previous relationship with another houseguest. Season 4 aka “The X-Factor” season, forced five houseguests to spend the summer with their exes. Jun brilliantly weaved her way through the game by laying low and cooking food for everyone. She’s the only one I can think of to actually gain weight while in the house. LMFAO. She and her on-again, off-again ally Alison, practically invented the “floater” strategy in the BB house. The two reality show frenemies would blow wherever the wind blew them. In the end, the two made it all the way to the finals, forcing the angry jury to award one of them $500,000. Why Jun wasn’t included in the the All-Stars Season, I’ll never know. On a side note, Season 4 also marked the first time two houseguests (David Lane and Amanda Craig) had sex within the house.

Season 14

Winner: 12. Ian Terry (left)
Should’ve Won: Ian Terry or Dan Gheesling (right)

Lame alliance name aside (Quack Pack), Ian proved himself to be a savvy player. I was 100% rooting for him once Frank got eliminated. He definitely blossomed to become one of the season’s most likable and memorable players. He knew when to be loyal and when to flip the script. Despite being betrayed, Ian knew it was better to work with Dan than against him. His only potential downfall was trusting Dan wholeheartedly (I blame him being BB starstruck). If he didn’t win at crucial times, he would’ve been blindsided like so many of his competitors. As with most reality shows, strategy and a little luck are the key to winning. As much as I wasn’t a Dan fan going into this season, I have to give the guy credit for saving himself during his hilarious funeral scam. That said, there is something innately skeezy about him that rubs me the wrong way, brilliant strategist or not. Another opinion that’s probably going to contradict most BB watchers is how ecstatic I was when Frank won America’s Choice. LOL. AH-MAZ-ING. The only thing better than him winning was if Jodi (first ouster) or Janelle took it home again. She wasn’t her best this season, but I still love the buxom blond bombshell.

Season 13

Winner: 11. Rachel Reilly (left)
Should’ve Won: Daniele Donato (right)

I’ll admit it, I was a Brenchel fan heading into this season. Sure, Rachel was a trainwreck and probably difficult to live with, but I admired her Big Brother awesomeness. She’s like Janelle (BB6 & BB7) but not as likable. Considering, she probably had the biggest target in the house due to her personality, it’s nothing short of a miracle that she’s in the Final 2. She should probably share some of that money with Adam, as it was his stupidness that allowed her to avoid elimination. Side note, if he really thinks he’s a candidate for All-Stars, he’s really delusional. I agree with Daniele’s assessment that he’s probably the lamest person to ever play the game. Speaking of Dani, I was definitely rooting for her. She also had a target but had less people working with her. Unfortunately for her, she got screwed this year by the “twists“. Both her and Kalia’s first HOHs were practically worthless. They both had to win HOH twice just to get the same person out- Dani with Brendon and Kalia with Jeff. But in most reality shows, a little luck is needed to win the game. Congrats to Rachel for taking it home. Next to Daniele, she was the vet I was rooting for (of course I was also hoping newbie Kalia would win as well).

Season 8

Winner: 10. “Evil Dick” Donato (left)
Should’ve Won: “Evil Dick” Donato (right)

Producers decided to throw two twists for Season 8. First, there was a houseguest in the house doing all of America’s bidding, known as “America’s Player“. The second involved three contestants who were brought into the house for having contentious relationships with three other houseguests. Evil Dick and his estranged daughter, Danielle were one of the pairs in the “Biggest Nemesis” season. Til this day, I’m amazed at Evil Dick’s game play. He practically threatened everyone in the house on a continual basis, forcing them to endure his constant bullying, insults and yelling. Love him or hate him, you have to applaud his strategy. Both his daughter and himself made it to the final two. Having said that, if it wasn’t for the “America’s Player” twist, he could’ve easily been voted out earlier. Luckily for him, America loved his antics and forced Eric (America’s Player and the deciding vote) to keep Evil Dick in the house and align with him.

Season 15

Winner: 9. Andy Herren (left)
Should’ve Won: Undecided (right)

I can’t believe Andy is our first ever openly-out winner. Why couldn’t it be the gay cowboy (BB 10′s Steven) who transitioned to porn instead ;) You might be surprised that I put Andy this high up on my list. I was never a fan and never rooted for him to win, but I have to give credit where credit is due. Dude was playing the game from the start… HARD. He stuck with one strong alliance and knew when it was time to cut them for another one. Plus, he was fantastic during the jury interrogation. He answered those questions brilliantly, especially the one about lying to everyone. Granted, his opponent had no grasp of the English language whatsoever which solidified his win. Poor GM. Hopes youse gets some help ;)

Now onto who should’ve won. That’s not an easy question to answer. I was never fully on anyone’s team this season. At one point, I rooted for Helen, Amanda, Aaryn, Elissa, Judd, Candice or Jessie to win it all, but each turned me off in some way or another. Either for their gross behavior, annoying habits, controversial comments or plain stupidity. It’s really sad that I couldn’t get behind anyone 100 percent. Hopefully, next season has more likeable contestants.

Season 11

Winner: 8. Jordan Lloyd (left)
Should’ve Won: Michele Noonan (right)

Jordan was probably one of the cutest and most likable BB players ever. But she was also one of the most clueless. Had it not been for her showmance and now real life partner, Jeff, she wouldn’t have lasted as long. This season featured one of the more well-thought out twists in the game. IMHO, “High School Cliques” was a brilliant idea. It forced some people to align with people they didn’t want to. It’s sorta fitting Jordan was in the popular clique, because in the end she won because she was more popular than that annoying rat, Natalie. However, if I had my way, nerdy Michele should’ve won it all. Her combination of awkward social skills and geekiness, with her intelligence and surprising athleticism made her a formidable foe. In fact, she was so formidable, they her voted out in the Final Four.

Season 3

Winner: 7. Lisa Donahue (left)
Should’ve Won: Danielle Reyes (right)

This season introduced the “Power of Veto” and was the only season to have every evicted houseguest vote for a winner. Season 3 is also noteworthy because it was the first time a previously evicted contestant was voted back into the game, which leads me to the only strategic move Lisa made. When her showmance partner was eligible to come back into the game, Lisa was smart enough to vote against him. She realized being in a relationship put a huge target on her back, and decided to vote for lovable Southern Amy instead. In the end, Lisa received all but one vote to win the entire game. Danielle Reyes was not just the runner-up, but the rightful winner of the season. She played everyone like pawns and did it with a smile on her face and a knife in her hand. Her only downfall, was her over-the-top (but hilarious) confessionals. Back then, every evicted houseguest was allowed to go back home and watch the aired shows. As expected the evictees became bitter and resentful of Danielle’s rants and cost her the game. Thankfully the producers realized that the voting contestants had to be shielded from watching the confessionals or else contestants in following seasons would severely censor themselves for fear of receiving a backlash. And that’s how the jury and “Sequester House” was born.

Season 5

Winner: 6. Drew Daniel (left)
Should’ve Won: Jennifer “Nakomis” Dedmo (right)

“Project DNA: Do Not Assume” was the twist for this season. It featured a set of twins playing the game as one. If they made it past a certain point, then both players were allowed to play by themselves. Besides the twin twist, the season also featured two long-lost siblings who didn’t know the other existed. For entertainment values, this was one of BB’s better ideas. The winner, Drew Daniel, was actually a twin himself, but not the set of twins in the game. Can you believe there are two of him? YUM. Drew was part of the first four-male alliance, “The Horsemen“. His ability to get along with everyone, control his showmance partner and utilize his athletic skills, helped him win the game. It also didn’t hurt to have one of the most annoying and awful players ever (Cowboy), as his competitor in the final two. If viewers got their way, Nakomis (coincidentally enough Cowboy’s long-lost sister.) should’ve won the half a million dollars. If it wasn’t for her, the term “backdooring” would’ve never been born. She quickly realized by not putting up the person you wanted out on the block initially, and nominating your friends as pawns would give the intended target a false sense of security. One of the best moments in the show ever, came as a result of this strategy. Jase, the person they wanted voted off, practically jizzed when his key was pulled out during that week’s nomination ceremony. PRICELESS. Even more priceless was when he realized days later he had been had and wasn’t safe after all.

Season 12

Winner: 5. Hayden Moss (left)
Should’ve Won: Britney Haynes(right)

In very few instances in Big Brother, let alone any reality competition show, the likelihood of an alliance starting from the start barely makes it all the way to the end. I wasn’t a big fan of the Brigade alliance, but I’ll give credit where credit is due. Sure, it didn’t make for compelling television. It’s far more interesting to see people backstab each other, but I can appreciate Hayden’s loyalty to his original alliance. Out of the foursome, Hayden was probably the best choice to take the crown, but I would’ve preferred the adorable Britney take the title. She didn’t just win me over, as evident by winning America’s Choice to receive $25,000. I also would’ve been okay with a Rachel win this season as well.

Season 10

Winner: 3. Dan Gheesling (left)
Should’ve Won: Jerry MacDonald (right)

Let me warn you, we’re getting into deeply hostile territory. None of the following winners even deserve to be in the same breath as any of the previous winners or should’ve beens. “Back to Basics” was the theme of this season and funny enough it would be oddly prophetic. Just like Season 1, there was absolutely no one in this cast I was rooting for. The only one I was remotely rooting for was Jessie, and only because he was a meathead and hilarious to make fun off. Everyone else was just awful. By “selecting” geriatric Jerry as my deserving winner, is my attempt at being ironic. He was the least worthy of the cast to win this season. This was one of two seasons, I actually had to Wikipedia to refresh my memory. Totally forgettable season. WASTE.OF.A.SUMMER. I know Dan is popular with our readers but I just don’t get the love. He redeemed himself in Season 14, but I’m still NOT a fan.

Season 7

Winner: 4. Mike Malin (left)
Should’ve Won: Janelle Pierzina (right)

The first All-Stars featured some of the best and most popular players ever to return to the game. Unfortunately for us, Mike Malin was one of those picked. Rumor has it, he wasn’t even on the short list to come back, but since he was BFFs with the great Dr. Will Kirby (Season 2 winner), the producers had to include him for fear of losing Kirby. Since he was neither popular nor deemed a brilliant strategist from before, he wasn’t considered a threat. Thereby practically guaranteeing him a spot in the finals. Unlike the most robbed player of the season, Janelle, who also happens to be my favorite contestant of all-time. The buxom blonde was targeted for eviction every week she was in there. If she hadn’t won either a POV or HOH each week, she would’ve been evicted. Against all odds, she managed to get to the Final Three only to be ousted again in the same spot as her original season. It’s sad one of the game’s most likable players lost to one of the game’s most hated.

Season 9

Winner: 2. Adam Jasinski (left)
Should’ve Won: Natalie Cunial (right)

Big Brother “‘Til Death Do You Part” was unique for several reasons. Due to the Writers’ Strike, this was the first and only season of BB to air in the Winter. CBS quickly ordered a new season to fill the void left by the strike. Secondly, it featured the most contestants ever. Thirdly it forced the players to play in couples for the first few weeks. Creatively and in terms of cast, this is the worst ever. BB implemented practically every twist possible in this season to keep it interesting. Two previous evicted housequests were allowed to return and two houseguests had a pre-existing relationship prior to entering the house. Adam was the worst possible choice to win this season. Not only did he continuously make fun of the people he was supposedly helping (mentally retarded individuals), but he was caught using his BB winnings to fund drug purchases and selling them. He now faces a maximum of 20 years behind bars, as well as a possible $1 million in fines. If a gun was held to my head to pick a rightful winner of this terrible season, it would have to be Natalie. She was annoying as f*ck, but she knew her Big Brother trivia and the game.

Worst Winner Ever

Season 6

Winner: 1. Maggie Ausburn (left)
Should’ve Won: Janelle Pierzina (right)

It’s ironic that the worst winner is from, what I think is the best Big Brother season ever. “Summer of Secrets” had the contestants playing in pairs. If their pair made it til the end, the winner would receive $1,000,000, doubling the previous winnings. This season had it all, major drama, fist fights, people you loathed and people you cheered for. “Nerd Herd“, “Bye, Bye, Bitches“, “Busted-Up Blonde“, “Janey Doll“, “Jack Shack” were some of the unforgettable catchphrases from this season. Maggie was a sound strategist, level-headed player and had excellent mind control powers. She was able to easily manipulate the “Nerd Herd” to do her biding while remaining out of the line of fire, for the most part. So why is she the worst winner? Duh, because she was boring and took the title from my beloved Janey. Just like in the All-Stars Season, Janelle was a target from the beginning. For some reason, women hated her and want her voted out. I loved watching her continually win competitions while the other women whined and cried in their corners. It made me laugh so many times. As mentioned earlier, Janelle is my favorite player of ALL-TIME and probably one of the best players ever to play the Big Brother Game. Easily one of the MOST ROBBED players in any reality competition show. LOVE YOU JANEY.

Who Is The Worst Big Brother Winner EVER?

View Results

Loading ... Loading ...

Phew that was exhausting. Do you agree with my assessment? Don’t you find most of the time the one you want to win, never ends up winning. Who’s your favorite or least favorite Big Brother winner?