Auckland lawyer Andrew Simpson is happily married, a father of five young children, and often would not charge clients if they could not afford his services. He'd help them anyway. Which is why his fall from grace is so puzzling to those who supported him in court this week.

Chalk and cheese. Standing together in the dock, Tyson Daniels and Andrew Simpson could not have been more different.

Daniels, tall and powerfully built, the 30-year-old vice president of the Comanchero motorcycle gang wearing a designer Versace top in the gang's colours of black and gold.

Simpson, tall and slender, a 42-year-old bespectacled lawyer wearing a bland grey suit, blue shirt and tie.

Daniels drove luxury cars; late model Range Rovers, Mercedes-Benz, Lamborghini and Rolls Royce vehicles.

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Simpson drove a seven-seater family van; a humble but practical way to ferry his wife of 16 years and their five children, aged 13 or younger, to church or school activities.

The men have virtually nothing in common. Nothing except they are now serving prison sentences for launderingg the vast profits creamed by the Comanchero gang through commercial drug importation and distribution.

"It is perplexing," said Guyon Foley, Simpson's lawyer, in trying to explain to Justice Gerard van Bohemen how his client found himself standing before the Court.

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Senior Comanchero Tyson Daniels, left, and lawyer Andrew Simpson stand in the dock together. Photo / Michael Craig
Senior Comanchero Tyson Daniels, left, and lawyer Andrew Simpson stand in the dock together. Photo / Michael Craig
Auckland lawyer Andrew Simpson was sentenced to prison for 2 years 9 months on money laundering charges. Photo / Michael Craig
Auckland lawyer Andrew Simpson was sentenced to prison for 2 years 9 months on money laundering charges. Photo / Michael Craig

It wasn't greed.

Although more than $1.4 million linked to the Comancheros was deposited into the trust account of Simpson's small law firm in working class Mt Roskill, he kept only $18,000 as payment for his time.

The money was distributed into other trusts Simpson established for Daniels, as well as other Comancheros or their associates, or sometimes payments were made directly to car dealers and real estate agents.

Simpson also advised them to keep any cash deposits under $10,000 to avoid raising red flags with the banks, which are obliged to report any transactions above the threshold.

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Foolishness, not selfishness or greed, was the reason for Simpson's astonishing fall from grace, according to Foley.

While Simpson had been suspicious about where the money had come from, Foley said a pair of "front men" for the Comancheros assured the lawyer the cash had nothing to do with drugs.

Their conversations about a shared Christian faith, church mission trips, and basketball pulled the wool over Simpson's eyes.

"He thought the money was from cash jobs for concrete pours," said Foley, referring to a contracting company linked to Daniels.

It was only later, around November 2018, when Simpson searched the internet that he realised his clients moved in the criminal circles of the Comanchero gang.

Only at that point, said Foley, could Simpson be considered reckless in handling the money.

"He asks for mercy."

The point about recklessness was rejected by Justice van Bohemen, who pointed out Simpson had repeatedly failed in fulfilling his duties to the court, as well as bringing the legal profession into disrepute.

The High Court judge cut the sentence imposed on Simpson because of his early guilty plea and previous good character, although the discounts were still not enough to qualify for home detention.

"You made it work. You set up the trusts and lended respectability, as a lawyer, to a criminal organisation," said Justice van Bohemen, in sentencing Simpson to 2 years 9 months in prison on the 13 money-laundering convictions.

"I deeply regret a father being separated from his family. However, that is a consequence of your decisions."

As someone who seemed unlikely to have a parking ticket, let alone a previous criminal record, prison will be difficult for a "clean skin" like Simpson.

Friends, family and clients wrote 20 letters of support for Simpson, all of whom were shocked and dismayed by his offending which was labelled "completely out of character".

Words like honourable, respectful, integrity, humble and patient were used to describe Simpson, who sometimes would not charge clients who couldn't afford his services.

If they needed help, he'd just do the work anyway.

"He was known as a good lawyer, an honest man, who consistently placed the interests of his clients ahead of his own," said Foley.

Comancheros vice president Tyson Daniels wears Versace top in gang colours of black and gold at his High Court sentencing. Photo / Michael Craig
Comancheros vice president Tyson Daniels wears Versace top in gang colours of black and gold at his High Court sentencing. Photo / Michael Craig

One of those clients, Daniels, was sentenced to four years and eight months in prison in the same High Court hearing after pleading guilty to nine charges of money laundering, participating in an organised criminal group.

The money-laundering offences came from purchasing a fleet of expensive vehicles.

There were four Range Rovers - with price tags of $175,000, $255,000, $218,000 and $280,000 - a $200,000 Mercedes-Benz, a Lamborghini for $285,000, and two Rolls-Royces which cost $364,000 and $595,000.

One of the Range Rovers seized by the police in Operation Nova, an investigation into the Comanchero gang. Photo / Supplied
One of the Range Rovers seized by the police in Operation Nova, an investigation into the Comanchero gang. Photo / Supplied

The luxury fleet was seized in April when police raided Daniels and other members of the Comancheros, as well as associates, following a year-long investigation codenamed Operation Nova.

Yet, just one month after his arrest, Daniels purchased another Mercedes-Benz for $215,000 while he was on bail and another $247,000 was found in the home.

While Daniels was not charged with any drug offences, Justice van Bohemen said the senior gang member played a crucial role overseeing the gang's operations for significant personal gain.

"You clearly knew the money was derived from significant importation of drugs."

Andrew Simpson outside the Auckland District Court after being charged in Operation Nova in April 2018. Photo / Sam Hurley
Andrew Simpson outside the Auckland District Court after being charged in Operation Nova in April 2018. Photo / Sam Hurley