The daughter of jailed earthmoving tsar Kevin Pollock faces a fight for her financial life after being ensnared in dealings by one of the businessman's closest associates.
Carina Lee-Anne Healey has failed in a campaign to overturn a $12 million-plus tax bill arising from share transfers carried out after Pollock's business empire began crumbling a decade ago.
In throwing out Ms Healey's appeal against the tax bill, the Full Court of the Federal Court has slammed her failure to call evidence from Pollock's business associate Joanne de Hollander.
Ms Healey is facing an application by the Commonwealth Bank for her to be bankrupted over an alleged $400,000-plus shortfall on a $2.1 million loan for an apartment at the Swan Brewery complex, which her father once called home.
Pollock is set to be in prison until at least late next year after being jailed in March, 2010, for swindling National Australia Bank of $3 million and then copping a further sentence for a $7 million tax fraud.
De Hollander was jailed for three years in July 2011, after pleading guilty to deception and fraud offences related to business activity statements.
The pair had worked closely together in Pollock's sprawling land development, earthmoving and garden centre empire, which rapidly grew early last decade but faced serious trouble in 2003 as NAB moved to unravel a previously strong relationship.
Despite parts of his empire falling under control of receivers trying to recover debts estimated at more than $50 million, other businesses linked to Pollock continued to flourish under his associates.
NAB's debt recovery campaign included an attempt to get control of a 48 per cent stake in Jandakot Airport Holdings Pty Ltd.
The stake was transferred between companies linked to De Hollander, ending up with a De Hollander-directed company that was trustee of trust that had Ms Healey as its beneficiary. The stake was sold in 2006 to the unrelated Ascot Capital group for $18.5 million.
The Tax Office claimed Ms Healey made a $14.2 million capital gain on the share sale for fiscal 2005-06. She was assessed as having a taxable income of $15.75 million that year, and was ruled as owing $7.4 million in tax and $5.4 million of penalties.
Rejecting her appeal, Full Court judges John Gilmour and Bruce Lander said there were too many features of the share transactions that were left unexplained by Ms Healey in her appeal.
"Ms De Hollander was a witness who was available and who could have shed relevant evidence on a dealing that was shrouded in mystery," the judges said.
Commonwealth Bank's bankruptcy application is due before the Federal Magistrates Court on February 4.