The ruling said Henderson's 2010 bankruptcy, his second, had been caused by personal guarantees given to cover company and associate's debts, and his inability to pay tax.
The ruling noted Henderson had borrowed extensively from finance companies in the run-up to the global financial crisis claiming personal equity of more than $30m.
The courts found Henderson did not beneficially own the assets underpinning these valuations.
"Mr Henderson accepts that he personally had none of the assets as represented when his 2006 - 2007 statements of position were completed," the ruling said.
Associate Judge Osborne noted Henderson had filed tax returns between 2001 and 2007 declaring he had received no income in any year.
The Associate Judge gave Henderson credit for "significant entrepreneurial skills," noting positive references from former Christchurch Mayors Sir Bob Parker and Garry Moore.
The latter said Henderson was a man with "1,000 ideas flowing around in his head at any one time [who] took on too much".
Commenting on the decision this afternoon, Henderson said:
"The judgment is quite mad. It is largely criticising me for giving personal guarantees in situations where I could not write a cheque if they were called upon. That is commercial naivety. That is exactly how the property development industry operates."
"The Government has spent millions of dollars trying to beat me through this process. Given that, there was always going to be a political outcome not a judicial one. This is exactly what this judgment is," he said.