Widow faces losing home of 56 years after city racked up $10K-a-day penalty

An 83-year-old Honolulu woman has filed a federal lawsuit against the city after being hit with nearly $600,000 in fines tied to what she says was an online rental listing error.

Sandra May, who has lived in her Honolulu home for 56 years, says the property has long been central to her family’s life. She raised her son there and depends on income from an attached apartment to help cover expenses on a fixed income.

In the newly filed complaint, May alleges that the City and County of Honolulu imposed penalties of $10,000 per day for almost two months because of a problem with her rental listing on a hosting platform.

Her attorney argues that a glitch in the platform’s system made it appear that the unit was available for short-term stays. However, the lawsuit says guests were not actually able to book the apartment for a short-term rental during that time.

Honolulu law prohibits homeowners outside designated resort areas from renting out or advertising residential properties for stays shorter than 30 days.

The lawsuit says the city sent May a notice of violation, but she did not see it right away because she was hospitalized after a serious car accident. By the time she returned home and was able to respond, the complaint says, the penalties had grown to $590,000.

When May contacted city officials to explain the medical emergency and rectify the listing, she said their only response was to tell her to hire a lawyer.

“It feels to me like they’re just trying to take my house, put me on the street with the rest of the homeless people,” May told Fox News Digital. “It’s very depressing, very upsetting.”

The city has placed a lien on her house and has blocked her from accessing basic government services, such as renewing her driver’s license or car registration, forcing her to find other methods of transportation.

May told Fox News Digital she cannot afford to pay such a heavy fine and that the thought of losing her treasured home of over 50 years is devastating.

“All the stress, the stomach problems, every day wondering if I’m gonna have a house… I was gonna live here for the rest of the days I have,” May said. “This is actually — I call this my little piece of paradise on earth. … The thought of losing it is — I can’t imagine.”

“It’s really frightening. I don’t want to be a burden on my son,” she added.

May’s legal team argues the massive penalty violates the Eighth Amendment, which shields against government fines that far outweigh the underlying offense.

“The Constitution prohibits excessive fines,” Loren Seehase, an attorney with Pacific Legal Foundation, told Fox News Digital. “Governments cannot simply impose fines that are so ruinous that they would financially devastate someone over a simple error. And that’s what we’re fighting for.”

Seehase noted that the case is part of a broader issue in Honolulu, where she said the city has issued more than $90 million in fines for similar advertising violations.

In Sandra’s case, she was in and out of the hospital, couldn’t get her mail, didn’t know about the violation, and it took her 59 days to correct it,” she continued. “And rather than having some sympathy and understanding that she was out of and in the hospital. They said, Well, we’re going to still fine her $590,000.”

The city of Honolulu said they could not comment on pending litigation.

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