Law Commons^™

Transaction-Specific Tax Reform In Three Steps: The Case Of Constructive Ownership, Thomas J. Brennan, David M. Schizer

Faculty Scholarship

Similar investments are often taxed differently, rendering our system less efficient and fair. In principle, fundamental reforms could solve this problem, but they face familiar obstacles. So instead of major surgery, Congress usually responds with a Band-Aid, denying favorable treatment to some transactions, while preserving it for others. These loophole-plugging rules have become a staple of tax reform in recent years. But unfortunately, they often are ineffective or even counterproductive. How can Congress do better? As a case study, we analyze Section 1260, which targets a tax-advantaged way to invest in hedge funds. This analysis is especially timely because a …

Toolkit For The Evaluation Of Crypto Tax Risks (Outline), Vincent Ooi

Research Collection Yong Pung How School Of Law

This Toolkit seeks to provide a practical, structured framework for the identification and assessment of crypto tax risks that can be used by tax administrations. It has three main parts. Firstly, an introduction to the Toolkit and how it should be used. Secondly, a series of questionnaires to complete. Thirdly, a commentary to provide additional context and details on each part of the Toolkit and its application. As tax administrations go through the questionnaires, they can rely on the Commentary to complement their existing knowledge and expertise to accurately identify the crypto tax risks facing their domestic tax systems.

Interlinking Between Income Tax, Citizenship And Democracy? A Case Study Of Canada And China, Jinyan Li

Conference Papers

The interlink between taxation, citizenship and democracy appears to be obvious in Western democracies: citizens are voters, taxpayers and beneficiaries of public spending funded by tax revenues. The literature on the politics of taxation suggests that democratic institutions affect taxation at every stage of the policy-making process, the type of elections and governance model influence the level of redistribution and complexity of the tax system, democracies generally choose policies that are more favorable to the poor than non-democracies, the tax mix varies with the nature of the political regime, and more repressive governments rely less on personal income taxation. Political …

'99-To-1’ Property Deals: Stamp Duty Avoidance Or Honest Mistake, Vincent Ooi

Research Collection Yong Pung How School Of Law

This article explains in detail the legal issues surrounding the recent ABSD audit and how exactly the general anti-avoidance rule and the stamp duty avoidance surcharge in the Stamp Duties Act 1929 can be invoked by the IRAS.The article highlights the fact that it may not be enough for a property buyer to show that the '99-to-1' holding was intended to enable the buyer to qualify for a home loan and not 'for stamp duty avoidance'. The property buyer must be able to answer the additional question of why the transfer of the property is 'staggered' in two stages and …

Solving The Valuation Challenge: The Ultra Method For Taxing Extreme Wealth, David Gamage, Brian Galle, Darien Shanske

Faculty Publications

Recent reporting based on leaked tax returns of the ultra-rich confirms what experts have long suspected: for the wealthiest Americans, paying taxes is mostly optional. Some of the country's richest have reported annual incomes that would be modest for a school teacher, even as the share of wealth held by the top .1% is at its highest in nearly a century.

Experts have long understood that one problem sits at the root cause of many of the tax system's failures to reach the very rich: valuation. Because it is difficult to appraise complex or unique assets, modern tax systems instead …

Tax Events In The Life Cycle Of Digital Tokens, Vincent Ooi

Research Collection Yong Pung How School Of Law

Digital tokens, or crypto assets, are digital financial assets based on distributed ledger technology. They come in a considerable variety of forms and have been used in a large number of different ways. Yet, relatively few tax laws of any jurisdiction mention digital tokens specifically. It is therefore necessary to consider how orthodox tax rules can be applied to transactions involving digital tokens. Given the broad range of forms which digital tokens and transactions involving them can take, this may appear to be a daunting task. A framework providing a rough guide on how to navigate this somewhat new area …

Report On The Challenges Which Digital Assets Pose For Tax Systems With A Special Focus On Developing Countries, Vincent Ooi

Research Collection Yong Pung How School Of Law

The paper highlights the need for governments to carefully consider the implications which the rise of crypto assets can have on tax systems, noting that the absence of a deliberate policy position would be a policy decision in itself, with consequences for the tax base. It discusses four main classes of tax risks which crypto assets pose.Firstly, crypto assets and crypto transactions can act as ‘functional substitutes’ for traditional assets and transactions. As existing tax laws are drafted without crypto assets in mind, this can produce a host of unintended tax consequences and produce opportunities for tax arbitrage.Secondly, the values …

Crypto Assets And The Problem Of Tax Classifications, Eric D. Chason

Faculty Publications

To date, Internal Revenue Service (I.R.S.) guidance on cryptocurrencies has been thin. When the I.R.S. has issued guidance, it occasionally mishandles the technical details (such as confusing air drops and hard forks). More personnel (and personnel with greater technical expertise) would allow the I.R.S. to keep pace with the explosive growth of cryptocurrency. Nevertheless, the I.R.S. could better leverage its existing resources by focusing on select issues and seeking enabling legislation from Congress. Specifically, the I.R.S. should focus on crypto issues occurring on a system-wide basis and not requiring taxpayer-specific considerations.

For example, determining whether Bitcoin is a “security” under …

Pink Tax And Other Tropes, Bridget J. Crawford

Elisabeth Haub School of Law Faculty Publications

Law reform advocates should be strategic in deploying tax tropes. Through an examination of five common tax phrases—the “nanny tax,” “death tax,” “soda tax,” “Black tax,” and “pink tax”—this Article demonstrates that tax rhetoric is more likely to influence law when used to describe specific economic injustices resulting from actual government duties, as opposed to figurative inequalities. In comparison, slogans describing figurative taxes are less likely to influence law and human behavior, even if they have descriptive force in both popular and academic literature as a short-hand for group-based disparities. This Article catalogues and evaluates what makes for effective tax …

The Income Tax, The Constitution, And The Unrealized Importance Of Helvering V. Griffiths, Lawrence Zelenak

Faculty Scholarship

The Supreme Court recently granted certiorari in Moore v. United States, for the purpose of deciding whether the realization doctrine remains a constitutional limitation on Congress's ability to impose an unapportioned income tax, as the Court held in its famous 1920 decision in Eisner v. Macomber. Although it is natural to look to 1920 and Macomber as the cause of today's uncertain scope of the congressional power to tax income, what did not happen in the Court's 1943 decision in Helvering v. Griffiths is as significant as what did happen in 1920. the presence of Moore on the Court's docket …

Virtual Worlds, Real Money: Tax Issues In The Metaverse, Vincent Ooi, Daryl Loy

Research Collection Yong Pung How School Of Law

When it comes to the tax world, the starting point is that international tax law does not currently give any special status to a meta realm as a distinct jurisdiction. The metaverse is not a term of art recognised by tax law. However, what we are likely to see is a change in business models and behavioural patterns, leading to different kinds of taxable events becoming either more or less prominent. Tax law may not inevitably change but the tax issues of the day will.In this article, we highlight three broad business models that are likely to feature prominently in …

Unplugging Heartbeat Trades And Reforming The Taxation Of Etfs, Jeffrey M. Colon

Faculty Scholarship

The much-touted tax efficiency of equity exchange traded funds (ETFs) has historically been built upon portfolios that track indices with low turnover and the tax exemption for in-kind distributions of appreciated property.

This rule permits ETFs to distribute appreciated shares tax-free to redeeming authorized participants (APs) and reduce a fund’s future capital gains. ETFs and APs, working together, exploit this rule in so-called heartbeat trades in which an ETF distributes shares of a specific company or companies to a redeeming AP, instead of a pro rata basket of the ETF’s portfolio. The distributed securities are appreciated shares of companies that …

A New Framework For Taxing Cryptocurrencies, Reuven S. Avi-Yonah, Mohanad Salaimi

Articles

This Article explores the tax law challenges associated with the taxation of cryptocurrencies and offers proposals to address such challenges. The Article addresses the proper tax treatment of different cryptocurrency transactions and activities. It examines various aspects associated with the taxation of cryptocurrency through its life cycle, starting from earning cryptocurrency, through its disposal or exchange. The Article also examines the tax treatment of two special crypto events, hard forks and airdrops. Specifically, this Article describes a proposal to tax cryptocurrencies based on their unique features. It argues that various ways of earning or receiving crypto tokens (for example, mining …

The Curious Case Of The 0.1 Per Cent Service Charge, Vincent Ooi

Research Collection Yong Pung How School Of Law

Just before 1 August 2022, a coffeeshop zi char chain announced that it would impose a 0.1% service charge. This decision was reversed within two weeks due to "customers' reactions".While the rate might appear to be absurdly low and not worth the trouble of imposing, this article suggests that there was more to the situation than first meets the eye. GST regulations require merchants to list GST inclusive prices unless the goods and services are provided by hotels and F&B outlets that are subject to a service charge. The 0.1% rate is thus explicable as a likely attempt to get …

What Web3 Means For Lawyers' Ethical Duties, Heidi L. Frostestad

College of Law Faculty Publications

Evolving technologies are one of the greatest issues of our time and continue to affect legal practice at a rapid rate, exponentially changing the structure of law firms and traditional practice.

Logan, Leland Hallowell, 1905-1980 (Mss 744), Manuscripts & Folklife Archives

MSS Finding Aids

Finding aid only for Manuscripts Collection 744. Correspondence and papers of Bowling Green, Kentucky attorney Leland H. Logan. Includes some personal material regarding his law practice and draft status, diaries for 1944 and 1945, and a small group of files representing his legal work, especially for the Home Owners’ Loan Corporation.

Green, Or Greed? A Fresh Perspective On The Valuation Of Conservation Easements, Alan L. Feld, Theodore S. Sims, Jacob Nielson

Faculty Scholarship

Charitable contributions of "conservation easements" have since 1980 allowed high-income taxpayers to shelter income from taxation through overvalued deductions. Overvaluation has increased dramatically in the past 20 years: a 2016 study of all easement decisions since 1980 reported that while overvaluation had averaged by a factor of two before 1994, it averaged by a factor of ten for decisions between 1994 and 2016. SOI data disclose that aggregate easement contributions deducted on Schedule A grew from $2.26 billion in 2015 to $6.5 billion in 2018 (the most recent year available). A recent report by supporters of conservation easements acknowledges that …

Tax Challenges In Debt Financing Involving Digital Tokens, Vincent Ooi

Research Collection Yong Pung How School Of Law

When digital tokens are used in debt finance, one cannot assume that the same orthodox tax treatment will apply. The highly specific nature of tax provisions means that they may apply very differently once digital tokens rather than fiat currency are involved. Through a case study of Singapore law, this article shows that if debt finance transactions involving digital tokens are not carefully structured, there may be severe tax consequences, including the inability to deduct borrowing costs or benefit from common tax incentives, and the possible incurrence of additional tax liabilities. This article submits that, under Singapore tax law, it …

Made Crypto Losses? Don't Assume The Taxman Will Subsidise You, Vincent Ooi, Vincent Ooi

Research Collection Yong Pung How School Of Law

The key points we made in the article are as follows:1) One might think that because income from transactions involving cryptocurrencies is taxable, the losses from such transactions would also be deductible. Unfortunately, the situation is not quite so straightforward.2) The key question is whether it is possible to establish that there was a trade or business (in trading cryptocurrencies). If so, then the deduction rules are a lot more generous. Otherwise, there will be quite a few restrictions:a) Losses from cryptocurrency transactions are unlikely to be useable to be set off against income from other sources.b) The losses will …

An Automation Tax- Adopt With Caution, Vincent Ooi

Research Collection Yong Pung How School Of Law

The post highlights three main issues that may result from the rapid and widespread automation of jobs: 1) declining tax revenues; 2) inequitable distribution of gains and losses from automation; and 3) social costs of job displacement, such as social support and retraining programmes for displaced workers.An automation tax may be imposed on a temporary basis to manage (slow) the rate of displacement of workers due to the adoption of automation technologies, but should not be a permanent feature. Otherwise, there will be a risk of loss of competitiveness in the long-term, possibly resulting in even greater economic harm.One main …

New Assets, (Largely) Same Old Rules: The Taxation Of Digital Tokens, Vincent Ooi

Research Collection Yong Pung How School Of Law

In this blog post, I highlight the fact that across jurisdictions, tax provisions specifically drafted to address the taxation of digital tokens are still quite rare, meaning that existing orthodox tax rules will have to be applied. However, care must be taken when applying tax provisions and one must be aware of the limits of "reasoning by analogy".Some tax provisions make reference to specific assets or asset classes and it cannot be assumed that digital tokens which look very similar to these assets will inevitably fall under those provisions. For example, no matter how much a digital payment token looks …

A Framework For Understanding The Taxation Of Digital Tokens, Vincent Ooi

Research Collection Yong Pung How School Of Law

As a relatively new area, the taxation of digital tokens can give rise to several dangerous misconceptions. This article lays out five propositions to counter these misconceptions: 1) digital tokens are not a single monolithic asset class attracting uniform tax treatment; 2) the common trichotomous division of digital tokens into payment, utility and security tokens is derived from securities regulation and should not be blindly adopted into tax law; 3) the three classes are not mutually exclusive and hybrid tokens may exist; 4) the fact that an asset is a digital token rarely changes its tax treatment by itself, which …

Taxation Of Automation And Artificial Intelligence As A Tool Of Labour Policy, Vincent Ooi, Glendon Goh

Research Collection Yong Pung How School Of Law

Rapid developments in automation technology pose a risk of mass displacement of human labour, resulting in the need to support and retrain displaced workers (a negative externality). We propose an “automation tax” that would slow the adoption of automation technology in appropriate circumstances, giving workers and social support systems time to adapt. This could be easily implemented through changes to the existing schedular system of depreciation/ capital allowances, reducing the uncertainty of its application and implementation costs. Such a system would be flexible enough to keep up with rapid technological developments. Two main dimensions may be adjusted to produce intended …

Tax Law Is An Ideal Subject For Advanced Legal Research, Kincaid C. Brown

Law Librarian Scholarship

Tax law is an ideal regulatory area for advanced legal research classes when you want to teach a comprehensive research topic putting together all of the various case, regulatory, legislative, and analytical sources that are needed in the real world. Since everyone pays taxes, tax is accessible and a good starting point to expend from the first-year common law focus, especially for those students resistant to regulatory research. Every regulatory area is different in terms of agency practice, resources, and the tools available, but tax law is an ideal example area because the tools used by law firms are great …

Incentivizing Innovation, Xuan-Thao Nguyen, Jeffrey A. Maine

Articles

This Article advocates for a new approach to incentivizing innovation through the design of ex post tax incentives for research and development (R&D) investment. In contrast to many nations, the United States relies largely on ex ante tax incentives, namely a tax deduction and tax credit for qualified R&D spending. Fundamental design flaws exist with these ex ante incentives; moreover, innovation occurs continuously and yields results at the back end of the innovation cycle. An appropriate framework should take into consideration the key players in the innovation landscape. These players are often treated differently under the tax laws such that …

Cryptocurrency, Legibility, And Taxation, Amanda Parsons

Publications

In Jarrett v. United States, a taxpayer in Tennessee is arguing that staking cryptocurrency did not result in him earning “income” under federal income tax law. This case illustrates the fundamental challenge that cryptocurrency and blockchain technology present for tax law. Wealth creation in the crypto space is not readily legible to the state. This absence of legibility threatens tax law’s reliance on placing economic activities into categories to determine how they should be taxed. Furthermore, this case highlights the harms Congress and Treasury are risking by not taking action on cryptocurrency taxation. The uncertainty and lack of guidance on …

Taxing Creativity, Jeffrey A. Maine

Faculty Publications

The recent sell offs of song catalogs by Bob Dylan, Stevie Nicks, Neil Young, and Mick Fleetwood for extraordinarily large sums of money raise questions about the law on creativity. While patent and copyright laws encourage a wide array of creative endeavors, tax laws governing monetization of creative works do not. The Songwriters Capital Gains Equity Act, in particular, solidifies creativity exceptionalism, exacerbates tax inequities among creators, and perpetuates racial disparities in the tax Code. This Article asserts that the law must encourage creativity from all creators. It is time to eliminate tax exceptionalism for musical compositions or expand its …

World Tax Policy In The World Tax Polity? An Event History Analysis Of Oecd/G20 Beps Inclusive Framework Membership, Shu-Yi Oei

Faculty Scholarship

The last decade has seen the emergence of a new global tax order spearheaded by the OECD and G20 and characterized by increased multilateral consensus and cooperation. This new order appears to reflect the emergence of a new “world tax polity” with shared structures, practices, and norms, which have been shaped through the work of the OECD, G20, and other global actors. But what are the pathways by which this new world tax polity has emerged?

Using event history regression methods, this Article investigates this question by studying membership in the OECD/G20 BEPS Inclusive Framework, a multilateral tax agreement among …

Taxing Creativity, Xuan-Thao Nguyen, Jeffrey A. Maine

Articles

The recent sell offs of song catalogs by Bob Dylan, Stevie Nicks, Neil Young, and Mick Fleetwood for extraordinarily large sums of money raise questions about the law on creativity. While patent and copyright laws encourage a wide array of creative endeavors, tax laws governing monetization of creative works do not. The Songwriters Capital Gains Equity Act, in particular, solidifies creativity exceptionalism, exacerbates tax inequities among creators, and perpetuates racial disparities in the tax Code. This Article asserts that the law must encourage creativity from all creators. It is time to eliminate tax exceptionalism for musical compositions or expand its …

The Parallel March Of The Ginis: How Does Taxation Relate To Inequality, And What Can Be Done About It?, Reuven S. Avi-Yonah

Articles

The United States currently has one of the highest levels of inequality among industrialized economies. In addition, numerous scholars have shown that social mobility in the United States is significantly lower than it was in the period between 1945 and 1970, when inequality was declining. The combination of these trends is dangerous because it risks transforming the United States into a society where small elites capture most of the gains, a pattern in which growth cannot be sustained over time. The level of inequality in the United States after taxes and transfers are taken into account is much lower, but …