Eric Watson has run out of trumps and the game is almost over.
Yesterday's High Court ruling that companies he owns are liable for $51.5 million in back-taxes plus interest (estimated at $60.5m) will be extremely hard for the once high-flying businessman to come back from.
Subject to appeal, the decision doesn't specify penalty interest which is likely to add millions more to the final figure.
The case, which centred on a complicated series of related-party loans using Cayman Islands vehicles to avoid paying tax, looks like the final chapter of a highly controversial business career spanning three decades.
It follows a well-publicised battle with Sir Owen Glenn, in which Watson came out the wrong side of, and previous fights with Josephine Grierson over Bendon and Greg Lancaster over Pacific Retail Group, to name a few.
There is now a big question mark over Watson's solvency.
Certainly his New Zealand-based Cullen Investments appears skint, following multiple claims on its assets.
This is evidenced by overseas documents relating to Bendon, since merged with Naked Brand Group, pointing out that Cullen is no longer a reliable source of funding due to changes to its financial circumstances.
And late last year the High Court heard that Watson himself claims he doesn't have the assets to pay Glenn the £29.1 million ($54m) which an English judge ordered him to hand over.
All this is severely damaging for Watson's modus operandi, which according to one judge, is to avoid bank finance and instead borrow from his business partners, while booking management fees from all his deals.
Indeed, it seems to me that Watson is someone who needs to be included on rich lists to give some semblance that he's worth the kind of money he displays with his flamboyant lifestyle.
His problem is that it appears that he's liquidated just about everything he can. Divestments include his luxury Te Hihi estate in Karaka, sold for $14m, a stake in Auckland restaurant Soul Bar and Bistro, for an undisclosed sum, and a half share in the New Zealand Warriors Rugby League team.
However, his remaining overseas assets are complicated and mostly illiquid.
Shareholdings in US companies Naked and Long Blockchain, previously Long Island Iced Tea, are now worth much less than they once were with both businesses underfunded and poorly performing.
Watson's real estate assets in the UK are now his main source of wealth although it has always been unclear as to what was actually his and what was tied up in partnership with Glenn.
Watson's ability to sail through controversy was best illustrated by the demise of Hanover Finance and its related companies which ended up costing investors north of $450m.
Co-founder Mark Hotchin bore the brunt of the fallout as he faced investors and the media, while Watson remained offshore.
At one investor briefing an elderly gentleman asked Hotchin where Watson was. He couldn't give an answer but later told TVNZ's Mark Sainsbury that the overriding factor was Watson didn't live here, he lived in England.
Yet Watson would appear in front of the cameras when he wanted to, whether it be at Warriors rugby league games or announcing his ill-fated partnership with Glenn.
While there may have been the odd win, there have been plenty of deals that have backfired.
During the drawn out Inland Revenue case, lawyers for Cullen Group argued the transaction in question wasn't intended to avoid tax, but rather required for Watson's relocation to the United Kingdom, where he needed to sever local ties in order to abandon New Zealand tax residency and qualify for non-domiciled status in London.
The judge rejected that argument.
Watson's camp now has to decide whether to appeal the decision.