I have met some of these young men(one as young 21 yrs old) who plan to spend most of their life in prison. Mostly because they've been in the system since they were young and its the only place they had any structure or discipline. I thought it was such a shame that that was all they could imagine for their lives.
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Yes, prison tends to fail as a deterrent after people spend much time there.
Among the criminal social milieu it can even be a reward of increased status.