When it comes to Big Brother, the best man doesn't always win. This is because when it comes to deciding who should win the grand prize, the jury votes for a variety of different reasons. Usually, it comes down to making big moves, winning competitions and keeping that jury happy so they don't vote against you.

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Today, we'll be taking a stroll down memory lane and looking at the ten most recent Big Brother winners. We'll be ranking them all on how much they deserved the win. Let's get into it with the least deserving person on the list. If you can't already guess who it is… come on you know you can.

Josh Martinez

Josh with his hands on his face after beating Paul in the Big Brother finale, Paul's hand up in the air in frustration.

Honestly Josh's win is offensive. Personally. Despite what literally everyone might think of Paul and his awful behavior in his second season, he played the game fantastically.

Josh's win was a 100% bitter jury situation. Sure, he weaponized that bitter jury to get himself the win, but Paul played circles around Josh, controlling him for most of the game. Josh had little to no agency in getting himself the win, the bitter jury did it for him. This is why he takes the bottom spot on this list.

Kaycee Clark

Kaycee Clark grins in a close-up on Big Brother

Kaycee is the fully upgraded model of Josh Martinez. Less horrible personality, tons of competition wins, power player and winner by a bitter jury. She ended up winning literally everything in the second half of the season (the poor Hive), and there's something to be said for that. Still, Tyler never lost control of the game, and even had the opposing alliance wanting to work with him.

When it comes down to it, social game is hugely important when it comes down to winning BB, and Tyler had it locked down. Well, he probably should have been a little bit nicer to Bayleigh.

Nicole Franzel

A promo photo for Big Brother featuring Nicole Franzel

Nicole managed to align herself with great people along the way, and Paul lost his first season due to a bitter jury too (he learned nothing did he). She didn't win much, but made good strategic decisions, turning on people left and right until she made her way to the final.

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She doesn't have the best track record, but an okay one that got her to the end, and that's what counts.

Ian Terry

Ian’s win is the most arguable out of the bottom three. He made plays, stayed under the radar, and won competitions when needed… but still, he was up against Nicole Gheesling’s brother, Dan.

Dan! This man held his own funeral and still has one of the most powerful social games of all time. Ian was good, but Dan is Dan. Ian isn't a bad player. He's simply outclassed by his runner-up, which earns him this low ranking on the list.

Steve Moses

Steve Moss Big Brother in blue shirt pale blue background

Steve had a good track record in his season. He played under the radar, but through his scampering little alliance, he managed to make power moves left and right, taking out powerful threats, including Vanessa, one of the most dangerous players that season. And dampest. When was she not crying?

He won competitions in the end when he needed to, and was always making strategic moves in the background, earning him this spot on the list.

Hayden Moss

Hayden from Big Brother, holding on to a rope and soaking wet.

Hayden Moss was part of one of the most powerful alliances in Big Brother history, The Brigade. This alliance was a huge reason he made it to the end, as they dominated the entire game, both through competitions and their many side alliances.

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He won four HOHs himself, and his strategic alignment with other power players took him to first place in the game, with the final three being comprised solely of Brigade members.

Rachel Reilly

Good Lord. Where to begin with this… well, let's start with a life vest. Rachel might have talked…a lot… both her seasons. However, she certainly was able to back it up. While she didn't do super great her first season, season 13 saw her win competition after competition, keeping her and her alliance safe week after week.

She was without a doubt the most dominant player in the game. She totally deserved her win for competition wins alone, but she certainly made important game moves that got her there too. Rachel is a great allround Big Brother player.

Andy Herren

Andy Herren on Big Brother

The most hated twink in Big Brother history, we have Andy Herren. This man turned on literally everyone in the game, and did it beautifully. He received no votes when he was on the block, and won himself the $500k.

It's certainly a feat to win with such a vicious social game. Hate him all you want, it is earned, but his sharp gameplay brought him to the end and won him the grand prize.

Jackson Michie

Jackson Michie Big Brother

Oh. You. Yeah, despite his… questionable behavior, it's factual that Michie is an incredibly good Big Brother player. His jury management was below decent, but he excelled everywhere else.

He won the most competitions in a season amongst men, and made massive social moves left and right to keep himself safe, along with showmance Holly. His huge lie that sent Tommy out the door is one of the most significant plays in recent BB memory. The two never lost control for a single second of the game, with much of that being due to his gameplay. As such, Michie is one of the best winners of the last ten seasons of Big Brother, if not all time.

Derrick Levasseur

Derrick Lavasseur smiling to the camera in Big Brother

Is there any competition for the #1 spot here? Derrick Levasseur ran every single part of BB16, and won with ease. This man literally evicted someone he planned on saving because she compared him to Dan (Nicole lol).

There was never an eviction that Derrick didn't want to happen, he ran the season from beginning to end. It's kind of ridiculous honestly. His social game is still unparalleled, and only a few players in the show's history can match Derrick, which earns him the number one spot on this list.

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