"All your offending involved a high level of premeditation where your actions were planned and deliberate involving . . . a sophisticated web of instruments," he said.
But the judge refused to impose a minimum period of imprisonment because the jail term was enough in itself to hold him accountable.
The ex-mayoral candidate has been on bail since charges were laid last year but will now swap his plush Ponsonby pad for a jail cell.
The most recent offences, which Swney admitted after a Serious Fraud Office investigation, involved dishonestly using 229 false invoices to obtain $2,527,005 from the organisation between February 2004 and October 2014.
In January, he pleaded guilty to four representative charges covering 12 years of offending and $1,757,147 of unpaid taxes.
"His motivation seems to be that he felt he had been underpaid for his contribution to HOTC and had not been sufficiently recognised and should have got more credit for building it into the successful organisation that it is," the Serious Fraud Office prosecutor said.
The court heard that Swney had sold a bach and raised $331,961 - 13 per cent of what he owes.
His lawyer Murray Gibson said there were ongoing discussions in a bid to raise more.
Heart of the City - a city-centre business association registered by Swney in 1994 - has income-tax exemption on the basis that it was created to develop or increase amenities for the Auckland public.
But technically the defendant was a contractor of the organisation as the sole director of AGS Services Limited and the services he provided were taxable.
A summary of facts filed by the IRD showed how Swney issued "various fictitious invoices" to Heart of the City, from which he benefited.
Investigators questioned several organisations - including the New Zealand Herald - over the authenticity of the invoices and determined they were created "without authorisation".
Swney is also on the end of a civil action launched by Heart of the City, whose board announced the move in December after forensic accountants scoured their finances.
The IRD welcomed the prison term handed down by Judge Fraser and said the defendant deliberately tried to "cheat the system" to avoid paying tax.
"Swney took every step to hide his actions. But due to the hard work of Inland Revenue's Investigators, he has been caught," Inland Revenue group tax counsel Graham Tubb said outside court.
"New Zealanders can be confident that we will catch people like Swney."
He said the department was already taking steps through the District Court to recover the stolen cash.Mr Gibson said the court should not lose sight of his client's achievements while at the helm of Heart of the City.
"He was an effective and hard-working spokesman for his organisation and through his efforts this city is a better place," he said.
Mr Gibson also highlighted the fact Swney was a "supportive son and devoted family man" to his partner and two children.
"You can sentence him secure in the knowledge he'll never be here again," he said.
Heart of the City Chairman Terry Gould said today's sentencing marked the conclusion of a "difficult, protracted episode" in the organisation's history.
The sentencing meant they could now move on with supporting members and the economic development of Auckland's CBD, Mr Gould said.
"I can confirm that the civil action process is still underway to recover as much of the stolen money as possible," he said.
Swney will be eligible for parole in less than two years.
Swney's timeline of events
1994 - Swney registers Heart of the City as an incorporated society and becomes chief executive
2007 - Fails in a bid to become Auckland mayor
Sept, 2011 - During a routine review IRD finds anomalies with a GST refund claimed by Heart of the City (HOTC). The invoice number does not match the name of the company and leads them to Swney
April, 2014 - He appears in Auckland District Court facing 39 tax evasion charges laid by the IRD
May, 2014 - Judge Grant Fraser suppresses Swney's name and that of HOTC
Sept, 2014- His contracted is terminated by HOTC
Oct, 2014 - Swney pleads not guilty to 39 charges laid by IRD and his name suppression lapses
Dec, 2014 - HOTC confirms an independent investigation had been completed and they would be pursuing the former CEO through civil proceedings
Jan, 2015 - Swney pleads guilty to four representative IRD charges covering $1.8m offending
Feb, 2015 - HOTC confirms seven events will miss out on funding because of costs incurred on investigative and legal efforts
April, 2015 - The Serious Fraud Office lays four charges alleging a decade of false invoices covering more than $2.5m. Swney pleads guilty to the charges
April, 2015 - The defendant gets a last-minute reprieve when Judge Fraser falls sick and postpones the scheduled sentencing
May, 2015 - The civil case between Swney and HOTC is called behind closed doors in the High Court at Auckland for the first time
June, 2015 - He is jailed for five years seven months for what the judge calls a "gross breach of trust".
June 26, 2015 - Swney will celebrate his 58th birthday on his third day in prison
