The construction company owed creditors more than $110 million.
The directors breached their directors' duties and were negligent in allowing the company to continue trading while insolvent.
The 178-page judgment said Mainzeal directors were reckless, "had adopted a policy of trading while insolvent", and "used money owed to trade operators, particularly sub-contractors, as working capital".
The directors also relied on assurances that the millions of dollars Mainzeal had lent to its China-based parent company Richina Pacific would be paid back if Mainzeal got into trouble.
"The assurances relied upon were ambiguous, conditional, and subject to the constraints of Chinese law, which restricted the ability to return money to New Zealand from China," the judgment said.
Justice Cooke decided on total compensation of $36 million, with Shipley and two other directors - Peter Gomm and Clive Tilby - expected to pay up to $6 million each. The rest must be made up by Richina founder and boss Richard Yan.
"The court arrived at a total figure of $36 million, being approximately one third of the total loss to creditors, and being similar to the balance of funds that the directors had allowed the shareholder group to extract from Mainzeal," the statement said.
Another director, former Brierley boss Paul Collins, was not ordered to pay any compensation, as he joined the Mainzeal board not long before its collapse.
Waiheke winery Isola Vineyards, an associated Richina company, which also received money from Mainzeal, was ordered to pay $2.1 million. Isola is in liquidation.
Justice Cooke ruled that Shipley, Tilby and Gomm had acted "in good faith and with honesty". However by adopting and sticking with a "vulnerable trading approach", they had jeopardised the company.
"It is likely that the Richina Pacific group would have taken steps to stop the vulnerable trading approach had the directors declined to agree to it, if necessary by threatening to resign," the court said.
Liquidators of the failed Mainzeal group of construction and building companies, Brian Mayo-Smith and Andrew Bethell of BDO, said the creditors had waited a long time for this day.
"We are thrilled with this judgment by the High Court which sets an important precedent for the required standards of corporate governance and care owed by company directors in New Zealand towards the company and creditors," Bethell said today.
"When the company collapsed in 2013, unpaid subcontractors and creditors were owed more than $115m. Many of these creditors themselves were put into serious financial difficulty as a result of the decisions made by the former directors.
"It has been a long, hard road to get to this point and, as a result of the court case and the damages awarded of $36m, creditors of the failed company will now receive some compensation for the losses they suffered.
"Directors have a responsibility to take into account the interests of creditors, existing and future, and not to allow a company to trade recklessly or incur obligations it cannot reasonably expect to be able to perform. This court case sought to hold the former directors liable for their actions in allowing Mainzeal to trade while insolvent and today's decision has recognised that negligence."
In addition, a further $2.1m was awarded to the liquidator in relation to other claims made by the liquidator, the statement said.
- additional reporting: BusinessDesk
