Many features of tax law can simplify the law in some senses for some taxpayers but make it more complex in other ways and for other taxpayers. This Essay focuses, in particular, on design choices that make the form of a transaction more determinative of tax consequences than its substance or that make tax law more rule like and less standard based. While such measures may simplify matters for taxpayers who contemplate tax law prior to acting (by making tax consequences more predictable), they can make the law more complex for taxpayers who do not attempt to ascertain the content of law prior to acting. As a result, these measures disadvantage unsophisticated taxpayers who are most in need of simplification.

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