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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 multi-billion dollar litigation is pending about this rule.

This Article proposes a three-step approach. First, when faced with a new type of tax planning, policymakers should decide whether a response is really necessary. How harmful is the transaction? How feasible is it to target this transaction without also burdening “good” transactions, which don’t involve the same abuse? This first phase determines what we call “the normative presumption” about the transaction.

Second, Congress should define which transactions are potentially problematic. An “initial filter” should exempt transactions that clearly don’t pose the relevant concern.

Third, once a transaction is deemed to be potentially problematic, a sophisticated test is needed to check whether it actually is. Admittedly, a sophisticated test is costly to administer. This is why initial filters are needed to limit how often it is used.

Along with proposing this three-part framework, this Article offers a novel critique of a sophisticated test the government has begun using: a “delta” test, which measures how closely investments track each other. Although delta is often considered the gold standard, we show how easy it is to manipulate. The trick is to add contingencies (e.g., so the investment terminates when the price reaches a specified level). To head off this gaming, we recommend an alternative test that focuses on value instead of on changes in value–and, more generally, on enduring features instead of temporary quirks.


Business Organizations Law | Law | Securities Law | Tax Law

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Creative Commons Attribution 4.0 International License
This work is licensed under a Creative Commons Attribution 4.0 International License.