Mr John George Russell holds a special place in New Zealand’s relatively brief tax history. He is a person who has challenged Inland Revenue’s authority and the taxing statutes more than any other individual. If Mr Russell had followed his father’s early advice and studied engineering he may have taken over the family farm on the outskirts of Hamilton and by now have been enjoying a peaceful retirement. Instead, his enjoyment of the accounting subjects taken at college, which he had enrolled into in error, ultimately led him to becoming a leading figure in the development of the then emerging New Zealand money market, and the managing director of the merchant bank Securitibank. Novel approaches to commercial issues and tenacity in litigation are the trademarks of Mr Russell, Auckland tax advisor and business consultant. Mr Russell is well known in New Zealand tax circles as the creator and defender of the ‘Russell tax template’, developed in the 1980s as a mechanism to turn the ‘water’ of taxable receipts into the ‘wine’ of untaxed gains. Template related issues are still being litigated some three decades later. There have been many cases related to the template covering both substantive and procedural issues. Mr Russell has had limited success on procedural grounds claiming his wins have been the result of good luck more than anything else. He strongly claims Inland Revenue have run a vendetta against him for many years. Inland Revenue have taken several different ‘Tracks’ when assessing various parties it considered received the tax advantage from the template. The ‘Tracks’ used to assess various parties are also regarded by Mr Russell as a vendetta tactic. Ultimately the litigation has led to ‘Track E’ with Inland Revenue personally assessing Mr Russell for tax, penalties and interest totalling in excess of NZD $200 million (underlying core tax of $15 million). A Court of Appeal decision found for Inland Revenue and confirmed Mr Russell’s personal tax assessment. Leave to the Supreme Court was not granted and Mr Russell has recently commented that a ‘Track F’ may now exist. Mr Russell has accused the Commissioner of Inland Revenue of fraud in respect of backdated assessments, and Inland Revenue have accused Mr Russell of fraud in relation to backdated documents. Mr Russell commented during one of our interviews when challenged about document backdating that “the only difference between an honest person and a dishonest one is often a date.” This thesis attempts to provide the reader with not only an overview of the litigation associated with Mr Russell, but also seeks to provide an insight into the person of Mr Russell. The Russell tax template was held to be a tax avoidance structure by the Privy Council in 2001. I did not intend to debate the merits of the Russell template with Mr Russell. One of the least known postures of Inland Revenue’s Compliance Model is that of the ‘game player’. It would appear that Mr Russell has many tendencies attributed to a person classified under this framework to be a classic game player. This thesis attempts to provide an in-depth overview of perhaps Inland Revenue’s most litigious taxpayer and asks whether Inland Revenue are now on ‘track’ to a conclusion. This thesis considers Mr Russell’s contribution to tax jurisprudence by looking at his journey over the last 30 years, giving the reader an insight into the life of Mr Russell.