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Caldwell was speaking at a press conference when he was heckled, and the sign language interpreter didn't miss a beat, performing a familiar hand gesture to sum up the passer-by's comment.
The Hawaiian city leader was trying to inform the public that a stay-at-home and work-from-home order that he'd put in place would continue for another two weeks in an attempt to stem the tide of new coronavirus cases.
He also announced that parks, beaches, and hiking trails would reopen for solo activities that include meditation, reading, jogging, and just having a lovely old sit down.
However, gatherings remain strictly banned.
Caldwell told the audience: "You can only get one household in one household. Your friends from another household are prohibited, or should not be coming to your house to gather.
"We're trying to really bring down the spread of the virus and we do know that it spreads when people from different households get together.
"You can't invite your auntie and [cousin] from another household over to your house to have dinner. That is a gathering that is prohibited."
It's tough, but we've all had to endure something like this at some point during this wretched year.
It seems that it's too tough for at least one person in the assembled crown, though.
Off camera, the person could be heard to shout the obscenity at Caldwell, and the sign language interpreter flung a middle finger to the sky to inform those watching with hearing impairments.
Obviously, this moment has garnered a lot of attention online since it happened, and whilst some have criticised the interpreter, a lot of people have argued that was her job to translate everything, which is exactly what she did.
For his part, Caldwell dealt with the situation fairly well, remarking that everyone is entitled to their view and has freedom of speech.
He went on: "I understand how upset people are, and I understand that from where they stand they see it as being unfair, but we're trying to be as fair as possible in terms of our public's health and safety."
Hawaii has seen 10,025 confirmed cases of coronavirus and 88 deaths since the pandemic began.
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