In the ancient world, a stranger who came to town was shunned by locals unless they could get a local to vouch for them, a local who would pay if the stranger misbehaved. Today we live in much larger societies, so maybe we should all have to get a rich insurer to "vouch" for us.
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The average "user" of the criminal justice system now is precisely the sort of person who wouldn't be able to afford your premiums under any realistic scheme, which makes it an especially bad place to implement this type of reform imho.
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Today we have parole and probation to make tradeoffs between safety and limited freedoms for such people. This system is a lot more flexible about such things. If we feel bad for them, we can redistribute more to them.
End of conversation
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