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I am not a fan at all of our prison system. He is a huge money drain and it has been largely privatized leading to multiple cases of judges issuing unwarranted jail sentences.
I am against the idea of locking people up as a punishment. Jails and prisons should be reserved for people who are a threat to society not as a place for "adult time-out". Locking up drug addicts and users for long periods of time is counterproductive and a huge waste of resources (along with the other victimless crimes). Violent criminals, of course, should be locked up and hopefully rehabilitated (something our current system doesn't do very well). Repeat offenders of petty theft and such should warrant some jail time. Non-violent drug offenders should be fined, if they are repeat offenders, then, rehab maybe. Locking them up does not protect the public, it doesn't help the drug user, nor is there any victim to give a sense of justice to. It accomplishes nothing. Granted, this is a gross over simplification of the situation but it is a short summary of the core idea.
From 1980 to 2003, the prison population increased by a factor of five. In 1980, it was just under 500,000 inmates. In 2003 there was 2,400,000 inmates. This is really weird because violent crime rates have been steadily decreasing or staying constant (depends on the category) over the last 30 years. Mandatory prison sentencing policies and "three strikes" laws have caused the explosion in prison population. "Three strike laws" have non-violent drug offenders serving life sentences when they should have had no jail time at all. Which borderlines on an 8th Amendment violation to me.
Then there is the corporate crime. Where people embezzle, extract, or screw people out hundreds of millions of dollars only to pay thousands of dollars of fines. That is a huge issue. Especially if lives were ruined because of it. But that is slightly off topic here.