That makes sense to a point. Example: John Smith gets arrested for possession. He gets released and is arrested for violating curfew. He gets released again and is arrested AGAIN for curfew. Third strike. Life sentence. He repeatedly broke the law, by your thinking, this is what he deserves.
5 Years later, Ted Johnson the child molester gets arrested and is sentenced to 15 years. He gets out in 4 because the jails are too crowded with John Smiths. Who would you rather walking around your neighborhood? John Smith the stoner without a watch or Ted Johnson the kid toucher? It makes no sense to lock up a person that has committed multiple victimless crimes which then in turn allows a monster to roam free because he only did it once.
Sometimes, and this is one of them, the rules are just plain stupid. There is a lot to learn about these so called good ideas. A lot of them, like sex offender registries, do way more harm then good. The core idea behind them is genuine, but they've been so manipulated and over reaching that they are now detrimental.