An Uber Eats driver paid $350 to have his car wheel released after parking for five minutes in a private Ponsonby car park while picking up an order.
In a video captured by a concerned member of the public the young man can be heard saying he was only making $5 for the delivery job.
The woman who took the video, who asked the Herald not to be named, said after she stopped filming she watched as he called a friend asking to transfer him some money.
She had intervened after driving past, seeing the two men having what seemed to be an altercation.
"I wish I could have helped him financially but I didn't have that much money in my bank account either to be honest," she said.
The driver had been parking in a Bashford Antiques car park, picking up food from a neighbouring Italian restaurant about 8pm on Friday.
The antiques store closes at 6pm, but its director Michael Organ clamped the man's wheel anyway, demanding $350 to release it.
Organ told the Herald five people lived in the building the shop was attached to, so it didn't matter that it was after hours.
He said he did not care that the Uber driver had to call a friend for money, saying he was sick of people affiliated with neighbouring restaurant Pane e Vino using his parks.
"If he is going to be earning a living driving then he is going to be respecting property rights full stop."
Organ accused Pane e Vino owner Tito Cucciniello of telling the Uber driver to park there, which Cucciniello denied.
"Of course I didn't ask nobody."
Cucciniello warned his customers and Uber drivers not to park at Bashford's in case they got clamped, he said.
The restaurant's website currently boasts a warning underneath its contact information saying diners parking there may end up paying $220 to have their wheel released.
The woman said she felt terrible she hadn't been able to help.
"Don't charge people $350 for parking there for five minutes. This poor guy," she can be heard saying in the video.
The footage includes several threats from Organ to call the police, which she invites him to do.
"I couldn't be bothered," he responds.
Organ also threatens to have a restraining order taken out against the woman for involving herself in the conversation, and tells the Uber driver it is illegal for her to be recording the conversation.
She says it is not illegal to record a conversation you are part of.
The driver protests that he is just doing a delivery job, but Organ doesn't budge, saying the man must pay the fee because "that's the law".
Wheel clamping on private property is currently regulated by a voluntary code of conduct rather than legislation.
Best practice says property owners should give drivers a 10-minute grace period, before issuing a breach notice which is similar to a parking ticket.
The code says clamping should only be used as a last resort but private car parking enforcers are not required to sign up to it.
An Uber spokeswoman said delivery drivers must park where it is safe and legal.
"We encourage restaurants to include pick-up instructions in the Uber Eats app for delivery partners to follow, which can sometimes include parking details.
"In this case, Pane e Vino has nominated two restaurant parks outside," she said.