I think (I'm pretty far away from all of this so this is just my impression) the point of these people, often poorly made and sometimes exaggerated, is that petty crimes (especially in a world where everyone is insured anyways so the actual damage is minimal) are not worth ruining human lives over. The American justice system is atrocious, with for profit prisons and extremely high recidivism rates, not to mention racial bias at many levels. Is it worth it to throw away a human life in that black whole over a bottle of wine?

In abstract both arguments (strict enforcement of all laws; and that the system's results are inhumane so lesser laws should be ignored) make surface level sense. A middle ground sounds best (some laws are loosened, leniency is used on first offenses, prison system reform to rehabilitate instead of punish, etc.).