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Abusive tax avoidance and tax evasion by high-income taxpayers pose unique threats to the tax system. These strategies undermine the tax system’s progressive features and distort its distributional burdens. Responses to this challenge generally fall within two categories: calls to increase IRS enforcement and “activity-based rules” targeting the specific strategies that enable tax avoidance and evasion by these taxpayers. Both of these responses, however, offer incomplete solutions to the problems of high-end noncompliance.

This Article presents the case for “progressive tax procedure”—means-based adjustments to the tax procedure rules for high-income taxpayers. In contrast to the activity-based rules in current law, progressive tax procedure would tailor rules to the economic circumstances of the actors rather than their activities. For example, under this approach, a high-income taxpayer would face higher tax penalty rates or longer periods where the IRS could assess tax deficiencies. Progressive tax procedure could also allow an exception for low-value tax underpayments, to avoid excessive IRS scrutiny or unduly burdensome rules for less serious offenses.

Progressive tax procedure could address the unique challenges posed by high-end tax noncompliance and equalize the effect of the tax procedure rules for taxpayers in varying economic circumstances. It could also complement the alternative approaches of increasing tax enforcement and activity-based rules while avoiding the limitations of relying exclusively on these responses.

After developing the normative case for progressive tax procedure, the Article illustrates how it could be applied in three specific areas: accuracy-related tax penalties, the reasonable cause defense, and the statute of limitations. These applications illuminate the basic design choices in implementing progressive tax procedure, including the types of rules that should be adjusted and the methods for designing these adjustments.

A substantial academic literature considers how agencies should interpret statutes. But few studies have considered how agencies actually do interpret statutes, and none has empirically compared the methodologies of agencies and courts in practice. This Article conducts such a comparison, using a newly created dataset of all Internal Revenue Service (IRS) publications ever released, along with an existing dataset of court decisions. It applies natural language processing, machine learning, and regression analysis to map methodological trends and to test whether particular authorities have developed unique cultures of statutory interpretation. 

It finds that, over time, the IRS has increasingly made rules on normative policy grounds (like fairness and efficiency) rather than merely producing rules based on the “best reading” of the relevant statute (under any interpretive theory, like purposivism or textualism). Moreover, when the IRS does focus on the statute, it has grown much more purposivist over time. In contrast, the Tax Court has not grown more normative and has followed the same trend toward textualism as most other courts. But although the Tax Court has become more broadly textualist, it prioritizes different interpretive tools than other courts, like Chevron deference and holistic-textual canons of interpretation. This suggests that each authority adopts its own flavor of textualism or purposivism. 

These findings complicate the literature on tax exceptionalism and the judicial nature of the Tax Court. They also inform ongoing debates about judicial deference and the future of doctrines like Chevron and Skidmore deference. Most broadly, they provide an empirical counterpoint to the existing theoretical literature on statutory interpretation by agencies. 

In the United States, nearly thirty-four million individuals provide informal care for their adult family members each year. Adult care recipients experience positive emotional and health-related outcomes when cared for by relatives, but this responsibility also places significant stress on caregivers. The government should subsidize and encourage family adult care, not only because of these social impacts, but also because this care can reduce healthcare costs. Family caregivers help their relatives avoid expensive institutional care and are also cost-efficient providers of care due to their relationships with the care recipients. The tax code is an effective and politically palatable vehicle through which the government can provide this subsidy, despite some structural limitations. However, existing and recently proposed tax incentives do not adequately target the benefits associated with family caregiving. Therefore, this Note proposes a new two-part advanced refundable tax credit that will help the government reduce costs and enhance social benefits.

Every year, billions of dollars are awarded as compensation for pain and suffering. A hard question—one that has vexed courts, legislators, and academics alike—is how we should tax them (if, indeed, we should tax them at all). In this Note, I articulate a new answer. If we take seriously the value of equality between injured people and uninjured people, we ought to tax compensatory damages for pain and suffering.

In Part I, I criticize an influential approach to the taxation of compensatory damages for pain and suffering. This approach appeals to various intuitive normative principles to justify exempting pain and suffering damages from tax. I argue that these principles are estranged from their normative foundations. Such principles are intuitive because they seem to embody an ideal of equality between injured people and uninjured people. But, as I show in Part I, equality does not always justify exempting pain and suffering damages from tax. Sometimes, a well-designed tax on pain and suffering damages serves equality better than an exemption does.

In Parts II and III, I determine which tax regime best respects the ideal of equality between the injured and the uninjured, giving that value neither too little nor too much weight. Following the optimal tax literature, I divide the work into two parts. First, I determine which tax policies would be best under the assumption that no one modifies their behavior in anticipation of tax consequences. To do this, I formulate an appropriate social welfare function, I estimate the relevant parameters, and I simulate optimal tax rates. I then consider whether the resulting taxes should be modified in light of behavioral responses that we should expect in the real world.

I conclude that we should tax some, and likely many, compensatory damages for pain and suffering—and we should do so at rates that increase with damages. Perhaps counterintuitively, this tax scheme is the best way of balancing the competing demands of creating well-being and distributing it equally.

Over the past several decades, Congress has turned increasingly to tax expenditures rather than to direct outlay programs to implement social welfare programs. Such a trend creates economic distortions and has proven disadvantageous to taxpayers in lower socioeconomic classes. The newest twist is in the area of disaster relief. Unprecedented before 2001, tax relief targeted to a disaster in a specific geographic region has now been established on two occasions-in the wake of the 9/11 attacks and in the aftermath of Hurricane Katrina. This Note argues that, in a disaster, both the vulnerability of lower-income taxpayers and the weaknesses of the Internal Revenue Code as an instrument for social programs are amplified. This problem was particularly acute after Hurricane Katrina. Congress should therefore reconsider the current trend toward using tax expenditures rather than direct relief in such situations, or alternately structure other relief to correct for its shortcomings.

Virtual worlds are increasing in commercial importance. As the economic value of computer-generated spaces soars, questions of how to apply our tax law to transactions within them will inevitably arise. In this Article, Professor Leandra Lederman argues for federal income tax treatment that reflects the differences between “game worlds” and “unscripted worlds,” arguing that the former should receive more favorable tax treatment than the latter. Specifically, she argues that transactions in game worlds such as World of Warcraft should not be taxed unless the player engages in a real-market sale or exchange. By contrast, in intentionally commodified virtual worlds such as Second Life, federal income tax law and policy counsel that in-world sales of virtual items be taxed regardless of whether the participant ever cashes out.

This Article offers a new understanding of the dynamic between the Supreme Court and Congress. It responds to an important literature that for several decades has misunderstood interbranch relations as continually fraught with antagonism and distrust. This unfriendly dynamic, many have argued, is evidenced by repeated congressional overrides of Supreme Court cases. While this claim is true in some circumstances, it ignores the friendly relations that exist between these two branches of government—relations that may be far more typical than scholars suspect.

This Article undertakes a comprehensive study of congressional responses to Supreme Court tax cases and makes a surprising finding: Overrides, although the main focus of the extant literature, account for just a small portion of the legislative activity responding to the Court. In fact, Congress is nearly as likely to support and affirm judicial decisionmaking through the codification of a case outcome as it is to reverse a decision through a legislative override. To investigate fully the nature of congressional oversight of Supreme Court decisionmaking, this Article undertakes both qualitative and quantitative analyses of different types of legislative review of Supreme Court decisions—examining codifications and citations, as well as overrides, in legislative debates, committees, and hearings. The result is a series of important and robust findings that challenge and build on the Court-Congress literature, identifying the legal, political, and economic factors that explain how and why legislators take notice of Supreme Court cases.

The study reveals a complex and nuanced interbranch dynamic and shows that the Justices themselves affect the legislative agenda to a greater extent than previously understood. This result challenges scholars who have questioned whether the Supreme Court should have jurisdiction over complex issues, such as those in the economic context, in which the Justices may lack sufficient training. This Article argues that scholars have little need to worry about Court decisionmaking in these areas: Not only do legislators routinely review the Court’s decisions, but they also frequently confirm the outcomes as valuable contributions to national policymaking via the codification process.