Exploring the difficulties of enforcing probation rules effectively, the high rates of recidivism among ex-convicts, and the concept of addiction to risk and thrill, including anecdotes of individuals slipping back into criminal behavior shortly after release and a man addicted to robbing grocery stores. The chapter also touches on proposed unconventional ideas to incentivize staying out of jail, the consequences of having a felony record on banking services, and the risks associated with banks making decisions based on politics or public perception.

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