A landmark prosecution by New Zealand Customs involving the biggest-ever interception of tobacco products marks the first time anyone prosecuted by Customs for fraud has gone to jail.
A months-long investigation by Newshub found the molasses tobacco import scam lasted almost five years.
Judge Robert Ronayne condemned Amar Shakib's crimes in the Auckland District Court on Monday.
"You referred to it as a stupid mistake. It was no stupid mistake, Mr Shakib - it went on for four-and-a-half years," he said.
The Iraq-born Aucklander made at least $330,000 by lying to Customs about the amount of shisha tobacco he was bringing in.
After a lengthy investigation Customs made their largest-ever tobacco seizure - 5.7 tonnes, with a retail value of $1.4 million.
"It's a fraud inquiry, so it's a huge amount of work. It was ongoing for 43 months," said Jamie Bamford from Customs' Intelligence.
Starting in 2009, Shakib placed orders with Al Fakher tobacco factory in the United Arab Emirates.
He would then ask for two invoices - one for the real value and one showing a smaller amount to show New Zealand Customs.
He would use these documents to lie to his local broker and his accountant.
It meant that for years the tobacco shipped or flown to Auckland was never properly accounted for.
Shakib's tobacco imports were almost always kept at Philpott's Airfreight until they were checked by Customs.
At the height of his offending, Shakib was trying to avoid paying $130,000 of tax and duties per importation.
Raiz Mohammed, who owns Kyber Food and Spices, bought more than $15,000 worth of shisha tobacco from Shakib.
"He was normal ... there was nothing special, or nothing that could be alarming, you know," he told Newshub.
Raiz said Shakib was the only person importing the popular Al Fakher brand.
"It's really popular, not only here but all different countries."
Shisha tobacco is increasingly popular in New Zealand and is subject to the same tax as normal cigarettes.
That's why by lying, Shakib was able to make so much money.
Shakib will now spend three years and four months behind bars.