It began with a handshake and progressed to legal fisticuffs, and this week Sir Owen Glenn emerged triumphant from a bruising struggle with fellow expat rich-lister Eric Watson in the silk-covered London High Court arena.

The sprawling case, ruled on by Sir Christopher Nugee in a 376-page judgment, covered meetings on yachts in The Bahamas, on golf courses in the Dominican Republic and in courtrooms in California, Nevis and London.

It chronicled the modus operandi of Watson - including his cultivation of personal relationships, use of opaque trust structures set up for "optical reasons," and a business run on the basis of no-money-down and lucrative management fees - that has seen him assemble his $420m fortune.

Watson himself was described by Nugee as being "courteous, well-prepared and smooth" when in the witness box - but also called his evidence unreliable and said he was satisfied he engaged in "deliberate deception".

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"I do not regard his evidence as trustworthy," Nugee wrote.

At the heart of the case was a struggle for control by Glenn of his fortune, particularly the proceeds his OTS Logistics business sold in 2012 to an Egyptian family for US$350m.

The judgment outlined how structures intended to safeguard this wealth from various international taxmen - trusts set up and run by Glenn's former business associated David Miller and Peter Dickson - went rogue and ultimately made £129m in investments in a joint-venture with Watson that Nugee ruled were inappropriate and should be unwound.

This dispute with Dickson and Miller, litigated in parallel in courts in Nevis and California, saw the pair turn off Glenn's funding tap in 2012, crimping philanthropic efforts and investments - including in a New Zealand tourist railway and a hitherto undisclosed film project chronicling the 1905 All Black "Originals" tour of Europe.

The London court heard Dickson and Miller had rewritten trust deeds, upped their pay rates to award themselves a combined US$6m in trustee fees, and become increasingly aligned with Watson as their dispute with Glenn escalated.

Legal action against Dickson and Miller was settled prior to the hearing of the London case, with Glenn reasserting control and replacing the pair with new trustees. This year's judgment covered hundreds of millions of dollars in investments made by the pair in 2012 - on behalf of Glenn's trusts - in what became known as Project Spartan.

The case covered meetings on yachts in The Bahamas. Photo / 123RF
The case covered meetings on yachts in The Bahamas. Photo / 123RF

Spartan was pitched by Watson and his advisers as a fabulous opportunity potentially worth billions to invest in English social housing stock - leasing them back to government - redeveloping distressed properties, and acquiring leasehold rents.

An initial £22.5m was said to be to buy out a partner of Watson's in a pre-existing property investment, but the court heard a large chunk of it - around £10m - was actually used to repay a loan for Watson's benefit.

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Around this time, Glenn's relationship with Miller and Dickson was breaking down and he was contemplating litigation in response - matters which affected Glenn's health - which he disclosed to his then-friend Watson while the pair were playing golf in the Dominican Republic.

Watson's offsider Miles Leahy told the court there were subsequent meetings where it was decided to focus on getting money transferred quickly to Project Spartan in advance of any litigation by Glenn.

"I think because of what was going on with Owen we were aware there were potential issues there and we wanted to get the capital safe, yes," Leahy said.

Nugee also heard Watson had later employed Miller's son at Bendon in Sydney, and tried to secure Dickson's university-age daughter secure a valuable legal training placement.

Nugee ruled the latter gave rise to a "realistic possibility of a conflict of interest" and set it as one of several grounds for unwinding the payments to Spartan.

While yesterday's judgment gives Glenn the win, the size of the purse is still uncertain.

Glenn's trust has already been repaid £130m, thanks to part-settlement part-way through trial, but is seeking an additional £52.8m to cover damages from having its funds tied up for years.

In a statement yesterday, the 78-year-old Glenn described the judgment as a "complete vindication". "Eric Watson has behaved appallingly."

Watson, through a spokesperson, refused to concede and flagged an intent to appeal and get back in the ring: "This is by no means over".