If in a game I can steal 10 points and at most get a 1 point penalty for getting caught, I'm much more likely to give it a shot than if I get a 10 or 20 point penalty for getting caught. Plus, if everyone else in the game is cheating and getting away with it, I'm much more likely to try it too.
The problem is if you make the penalties so severe and the application of the rules unequal, then you end up with chopping people's hands off for stealing.
I'm sure there are tons of people that would be willing to risk a month or even a year in Club Fed for a chance at set for life money.
The calculation is different for everyone.
It would be a much better deterrent to know that if a crime were committed, the punishment came swiftly: the threat of (almost) immediate jail time is much more powerful than the maybe (your life is over).
Again, if a society truly valued freedom, just losing that would be such a great punishment. When you say that such a punishment is not enough its precisely because you dont value freedom that highly.
What brought me to this path was the simple thought exercise: should escaping jail be illegal? How can it be illegal if it is a fundamentally moral act?
Prisons aren't mainly intended to deter crime, they are for satisfying the public's vengeance lust and to divert taxpayer funds to cronies of government officials.
Prison should not be cruel (e.g., solitary confinement for more than a short period of time in unacceptable), but it should still be unpleasant if it is to serve as a deterrent to committing crime, and that is definitely one of the biggest reasons we have prisons... to incentivize people to stay out of them.