alt Hacker NewsSure, but that's an entirely different metric to judge him on than the comment I was replying to. Instead of trying to judge the heinousness of his crime by comparing the raw amount stolen ($20-35B) to the value of a human life ($10M), you're judging based on the number of times a crime is committed. That makes intuitive sense; more crimes committed gets a harsher punishment.
The hypothetical is there to try to tease out a principled stance from our intuition. If someone stole a wallet that contained $1B, should their punishment be a million times harsher than someone who stole a wallet with $1000? Should it be 5x harsher? The same punishment?
If your stance is that luck would not ideally affect one's punishment then the amount stolen isn't itself a factor in determining the punishment. It's downstream of the true factors, such as the number of thefts committed. The amount stolen is correlated but not causal.
> If your stance is that luck would not ideally affect one's punishment
I don't think this is generally the stance. If you give someone a little shove, they bump their head, and they get a bruise, you've committed assault, you're facing up to a few months in jail. If you give someone a little shove, they bump their head, and they die, you've committed murder, you're facing potentially years in jail. According to the eggshell skull legal doctrine[0], it doesn't matter that some people are especially more vulnerable than others (ie that you were particularly unlucky and pushed someone who happened to have an eggshell skull), you take responsibility for the consequences when you do something illegal.
Now in our world, no one is going to steal a wallet with $1 billion in it - there is some reasonable assumption that when taking a wallet you are at most stealing a few thousand dollars, and never more money than a person would be comfortable keeping in their wallet. While that's against society's rules for various reasons, it's not a particularly damaging crime. The victim will be perhaps very inconvenienced, but no worse.
However if we lived in a world where a wallet might contain 1 billion dollars, that would be a different story. Now you might very well be causing life altering damage to large numbers of people when you steal a wallet. The decision to do so, knowing the risk, is a much more serious offense. The metaphorical wallet Madoff stole was not only possibly filled with an enormous sum of money, it very likely contained that much. Beyond the much greater and repeated effort that Madoff employed to steal this money than would be needed to snatch a wallet, the very fact he was willing to cause so much potential damage for his personal gain is a much more severe breach of the social contract than a petty thief.
There definitely shouldn't be a simple linear relationship of dollars stolen to days in prison; but that doesn't mean the punishment should be completely agnostic either. These relationships are complex and need to be looked at in context with other relevant factors like pre-meditative effort or degree of remorse. Regardless of one's stance on rehabilitative vs punitive justice, I think we can all agree someone who effortlessly broke core parts of the social contract and would gladly do so again needs to be treated differently from someone who made a bad call in a moment of weakness.
[0] https://en.wikipedia.org/wiki/Eggshell_skull