Interestingly, Canada has had relatively little recent experience with anything like the heated concerns expressed in American and EU tax policy circles regarding excessive compliance costs of corporate income taxes. The lack of debate regarding compliance costs cannot be attributed to a...

This article analyzes the economic benefits and costs of the income trust vehicle for entrepreneurs organizing their business affairs. In doing so it examines the precise nature of the relationships between capital structure, income taxes and income trusts, reaching the conclusion that neither...

This paper examines how justices on the Supreme Court of Canada voted in Charter appeals between 2000 and 2009. Charter appeals, at least in popular belief (and possibly also in theory), have the greatest potential to reveal voting that is influenced by extra-legal policy preferences. Confining...

The question of whether gains or losses on the sale of real estate should be treated on account of ordinary income or capital gains is particularly relevant for individual taxpayers, since capital gains are taxed at a lower rate than ordinary income. ‘‘Capital assets'' are defined by...

The federal tax code states that in order for a transaction to be recognized for tax purposes, it must pass a two-pronged "economic substance" test (Section 7701(o)(1)). If a transaction has no purpose or effect beyond generating tax savings for the parties involved, it lacks economic substance....

Like many legal questions, the question of whether a financial instrument is more debt-like or more equity-like can be thought of as a binary classification problem. If researchers can harness enough information from the body of legal decisions, these tools can provide an accurate prediction for...

Advance tax rulings are an increasingly common feature of mature income tax systems throughout the world. The Organisation for Economic Co-operation and Development's (OECD's) work demonstrates that there has been a trend from 1990 to 2013 among OECD member countries to adopt advance tax rulings...

We use machine-learning models to analyze and anticipate the outcome of the IRS’s appeal of the Tax Court's decision in Cross Refined Coal LLC v. Commissioner, No. 19502-17 (2019) (bench op.). We predict that the D.C. Circuit will hold that the taxpayer had been carrying on a partnership...

In this article, we explore how tax experts can use machine learning tools to safely test and assess potential litigation strategies before deploying them at trial or on appeal. This can be especially useful for cases involving questions of law that turn on interrelated factors, such as the step...