"As a result of the audit, the SII found the 2008 loan was a hidden distribution of profits and recharacterised the loan under the Chilean tax laws," the ruling said.
Rank settled the tax investigation in April 2011 in a deal that saw 93 per cent of interest and penalties waived, and $14m was paid to SII.
Hart's Rank Group had launched the legal action in New York in 2012 arguing the takeover deal included provisions indemnifying it from tax payments - meaning Alcoa's former owners were liable for the payment.
Judge Broderick ruled the loan was agreed at the time of Rank's takeover to be an assumed liability varying a $10m deferred tax liability.
According to Forbes rich-list rankings Hart should be able to take the ruling in stride. Since the Alcoa deal a decade ago he has doubled his net worth, and is now by some margin New Zealand's richest man with a valuation of $14b.
Requests for comment by the Herald sent to Rank Group's headquarters in Auckland went unanswered this morning.