Troper8909: The fact that none of the winners get to keep 100% of their money. In Island, Owen gives up the $100,000 for the chance to win $1,000,000. Nobody actually wins this money so it gets carried over to the next season. In the Celebrity Manhunt Total Drama Reunion Special it is stated that Beth bought a holiday for her and Lindsay in France with some of her prize money. The two of them accidentally defaced the Mona Lisa and got put in jail. Beth's parents used the rest of the money to bail them out of jail. In World Tour Ezekiel steals the money from Heather then jumps into the volcano burning the prize money. In Revenge Of The Island Cameron decides he doesn't know what to spend the money on so he splits it between the other contestants. Sure he did it willingly but he still didn't keep it. In All Stars the winner isn't shown losing the money but the $1,000,000 probably got lost when the island sinks. Finally, in Pakithew Island Shawn splits the money 50:50 with Jasmine. Again, he was willing to do this but this does mean he wouldn't be able to build his zombie-proof house. The fact that the winners put all of this work in throughout the series to come out on top, mostly for nothing, is pretty unfair.
Some_Person: Starting in World Tour the writers went a little too far with the comeuppance of the antagonists. In World Tour Blaineley broke every bone in her body leaving her in a full body cast being unable to talk or move. Alejandro got run over by the cast and then covered in lava leaving him so injured he is put in a robot suit unable to speak for a whole year. In Revenge of the Island Scott got mauled by Fang leaving him unable to talk or move with out a trauma chair. Oh, and to make things more cruel the rest of the contestants (even Dawn and Brick) laugh at him. Next in All-Stars Duncan was arrested for blowing up Chris' cottage and according to Chris he is now going to "Big Boy Prison". Then Courtney lost her new best friend and boyfriend and no one missed her after she left. And in an exclusive clip two sharks throw up on her. She probably got the least cruel comeuppance but seeing as she didn't do to many villainous things that season it felt rather undeserved. And finally in Pahkitew Island Dave was left on the island alone with a very angry Scuba Bear
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General
These examples cover multiple moments. The second covers at least four or five and the first covers six. Please choose one moment to use before putting it back on. Also, given the nature of this page, I don't think a general section would be necessary or allowed.