Genuinely interesting, however i would recommend expanding on the torturous feeling of having to chose between ones life and entire fortune in as short a window as 5 minutes, describing the mental anguish, perhaps telling the reader how the man earned his wealth (i do not know his true story for one) perhaps for the sake of the story describing how he hungered in his youth, or perhaps had a mind for business and not having the possibility of starting a financial venture and painstakingly saving every copper to open his business and now being forced to chose between his life's work or his life. Make the reader understand what the man is experiencing, it is after all a horror story, make us feel his mental anguish, and pain, his dread at the idea of being crushed by a gigantic trash compactor, his life ending in but an instant as the gargantuan metal walls crush him like so many insects.
I believe that the emphasis on the choice is arch-important, the fact the man is faced with a decision that no one ever thinks he must make, and just what happens to a man's brain, what races in his mind, as he must do that.
If i may add another thing it is the fact that a character must be relateable, the reader must feel some remorse for the man, so that he can i a way feel what the character feels, consider the following two instances:
1) A man died of a stroke
2) A kind man, loving father of 3 and caring grandfather of 8, a man who's name could never be associated with any misdemeanor of any kind, a man who shared what he had with others and never expected anything in return died this morning of a stroke, his large grieving family is devastated, so too are his neighbors and friends.
For whom did you feel more remorse? the man of whom you know nothing, or the man of whom whom you know much? now if those two men were tortured, as they often are in Saw, for whom would you care more? the latter ofcourse, once you make the character relateable, even if you reveal him as scum later, the reader will pity him or feel the need for righteous punishment for him, depending on how you develop the situation.