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Philosophically interesting, but I'm not sure it really serves all the purposes prison has. There are four widely recognized ones: retribution, discouragement of crime, protection of society (via isolation of harmful members), and rehabilitation. A short period of intense suffering, even supposing you could inflict an equivalent amount of "pain units", only addresses retribution and discouragement of crime.

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As for protection of society, I don't think Ross Ulbricht would be a threat to society if he were released now. He is in prison mainly to serve as an example to others. There are probably a lot of other people like him in prison.

As for rehabilitation, I would think that in most cases it could be better accomplished via a community based program. For example, drug rehab works better in drug treatment facilities than in prison.

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Sure, I'm not speaking specifically of Ross' case, but the general case of prisoners preferring a quick, extreme punishment to a drawn out, mild punishment.

I agree that Ross is not someone who is a serious reoffender risk. OTOH, justice professionals might feel differently based on his lack of contrition (this typically counts against convicts at sentencing, partly because there's a view that it says something about recidivism risk). https://fortune.com/2015/06/01/why-a-judge-threw-the-book-at...