!!The film:

* Ben Richards only relents to Killian's request to enter the game when he threatens to send his fellow escapees in his stead. They double-cross him and send them in alongside him regardless.
* "[[FamousLastWords I don't want to be the only asshole in Heaven.]]"
* All the shows previous... ''winners''.
** This could be mitigated somewhat when you consider that, unlike Richards, some of those men were probably ''not'' innocent. However given what is considered a crime under this regime, even actually being guilty doesn't necessarily make them evil criminals deserving of such a fate.
** Lets also remember the audience believed these men had been pardoned by the hellish experience, only to be murdered off-camera.

!!The book:

* Holy crap, where to begin. For starters, you've got Richards' only option to save his wife and child being entered into the contest, a certain death sentence for him.
* And then you've got the little girl dying of lung cancer. By the time Richards comes along, the disease has spread from her lungs and into her belly. Her family has no choice but to keep her doped up to at least dull her agony while she slowly wastes away.
* Elton's [[spoiler: death. Made even worse by the fact that it was caused by his senile mother calling the cops on Richards.]]
* But the king of them all has to be [[spoiler: when Richards finds out about his family's death. All of his hope, all of his reasons for entering the contest, or even keeping himself alive comes crashing down in those few moments. The man has literally ''nothing left to live for.'' The revelation sends Richards into a HeroicBSOD and is what ultimately makes him decide to take down the Games Corporation once and for all.]]