Mayor Caldwell is trying to seriously ramp up his "compassionate disruption" tactics on homelessness.
He's pushing two new laws: One bars anyone from blocking a sidewalk anywhere on Oahu between 6 am and 10 pm. The other makes it illegal to live in a public space when shelter is available.
The mayor knows he is picking a fight with civil liberties advocates over these measures. The ACLU said the proposals amount to an island-wide sit lie law, which might be unconstitutional. They argue that the proposals clearly target unsheltered people.
While the ACLU has usually prevailed in these kinds of lawsuits against the city, this might be a fight worth taking for the mayor.
In the years since compassionate disruption has begun, most of the people who are homeless for economic reasons seem to have found shelter.
Those remaining on the street are usually chronic. If not mentally ill or drug addicted, they stubbornly cling to a lifestyle that is a blight on the larger community.
This is a much less sympathetic population than those that occupied kakaako three years ago.
Perhaps the courts will agree that compassion can only go so far and a little more disruption is called for.
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