Over the past four years, city attorneys have warned Mayor Kirk Caldwell and the City Council not to enact laws that would place a ban on sitting and lying on Oahu sidewalks because they did not think they could stand up to constitutional challenges.

But now Corporation Counsel Donna Leong, the city’s top civil lawyer, is placing her support behind two new measures introduced by Caldwell that do essentially the same thing islandwide.

City officials insist the measures are about keeping sidewalks clear for pedestrians and not penalizing the homeless, but it’s clearly those who camp on city sidewalks who are most adversely affected by the prohibitions.

“Obviously, (the bills) are designed to keep the homeless from setting up homes on the sidewalk,” said attorney Robert Thomas, who specializes in land use law.

The two bills were formally numbered by the city clerk’s office Thursday. Specifically:

>> Bill 51, the “sidewalk obstruction” bill, which would make it illegal for people to obstruct city sidewalks anywhere on the island from 6 a.m. to 10 p.m. daily if it interferes with the normal flow of pedestrian traffic. The offense would be considered a misdemeanor subject to a $100 fine or community service.

>> Bill 52, the “lodging” bill, which would prohibit “lodging” on city sidewalks or other public areas in all parts of the island at all hours. To lodge, as defined in the bill, is “to occupy a place temporarily; to sleep; to come to rest and refuse to vacate” an area when requested by authorities. Before issuing a citation, an enforcement officer would need to check to see whether there is available shelter space nearby that a person being removed can sleep.

Both bills will get their first airing at the City Council’s 10 a.m. meeting Wednesday in Kapolei. Assuming they get the first of three necessary approvals that day, they will go to the Public Works, Infrastructure and Sustainability Committee, chaired by Councilwoman Carol Fukunaga.

Leong, through a city spokesman, said Thursday she is holding off commenting on the bills until they get a hearing.

Thomas, who specializes in land use law, said it appears city lawyers have taken great pains to craft the bills with language that works around areas that federal courts have found unacceptable.

“They’ve put in what might be considered safety valves in there to keep them from a successful challenge,” Thomas said. The obstruction bill is similar to the sit-lie bill, “but there are some key distinctions” which might make it tougher for a challenge to be successful, he said.

The argument against an islandwide ban in the past has been that a blanket ban on sidewalk dwelling and storing amounts to discriminating against homelessness, making it unconstitutional. The courts have concluded generally that municipalities can, in the interest of public safety and health, regulate conduct, but not on status or speech, Thomas said.

The new obstruction bill takes the prohibition off during certain hours of the day, thus taking away the argument that it is a blanket ban on sleeping on the sidewalks or criminalizing homelessness, Thomas said.

And while the sit-lie bans are misdemeanors, the obstruction bill leads to a civil violation resulting in a fine or civil service, he said.

As for the lodging bill, “there has to be a place for you to go under this bill” before a person can be removed from the sidewalk, he said.

Thomas said he expects the bills, if they become law, to be challenged. “Now if I had to put money on it, I’d say that there is a better chance than not that they would stand up,” he said. “Of course, a lot of it depends on a particular situation — and how they’re enforced.”

Joshua Wisch, executive director of the American Civil Liberties Union of Hawaii, said his organization has serious issues with both bills.

“Everyone wants to find a way to deal with the housing crisis, but the ACLU of Hawaii has an obligation to ensure that as government pursues new policies, it does so without violating peoples’ civil rights,” Wisch said in a statement. “And it is clear that the bills submitted to the Council today target people who are unsheltered. We will be closely watching as these bills are considered and amended by the Council and will decide during that process whether a legal challenge will be necessary if either bill is signed into law.”

The ACLU took the city to court over its handling of the belongings of people swept from city sidewalks under the sidewalk nuisance and stored property ordinances, which led to the city agreeing to changes in the retrieval, storage and disposal of property.

The obstruction bill “makes illegal simple human activity, all across the island for a huge portion of the day,” Wisch said. “While certain exceptions like those for expressive activity are welcome additions, it seems likely that this bill will be enforced in a way to target only unsheltered people.”

The illegal-lodging bill acknowledges that shelter space needs to be made available before the city can remove someone from the sidewalk, Wisch said. But it does not consider that some shelters don’t accept families or pets, have residency time limits that may be too short or charge fees that some cannot afford, he said.

At least four Council members said they are eager to consider an islandwide ban, arguing that the piecemeal sit-lie bans apply in pockets of the city and serve only to drive the homeless from one neighborhood to another.

Fukunaga, whose committee is expected to hear the measures, said the position of most Council members has been consistent since Caldwell introduced his first sit-lie ban prohibiting sitting and lying on Waikiki sidewalks in 2014.

“We should have people be able to traverse sidewalks and be safe in city parks and recreational areas throughout the entire island, as well as having meaningful homeless solutions — treatments, services and whatever that combination is within each Council district.”

Finding shelter and services for the homeless is as important as the sidewalk prohibitions, she said.

Councilwoman Ann Kobayashi said it’s unfair that people are being prohibited or intimidated from using certain sidewalks, parks and other facilities.

Crane Park, at Kapahulu and Kaimuki avenues, is now so overrun with campers and their stuff that many constituents have stopped going there, Kobayashi said. Some community sports leagues have even stopped holding games there, she said.

Ikaika Anderson and Ernie Martin, who both have unsuccessfully introduced bills for islandwide sit-lie bans after strong objections from Leong’s office, also said they are pleased Caldwell is now employing an all-Oahu strategy.