Are capital gains the Achilles’ heel of taxing the rich?

This paper considers the role of capital gains taxation in enhancing tax progressivity, and argues that capital gains are the Achilles’ heel of taxing the rich more effectively. We revisit the key aspects of how capital gains are taxed and address the main arguments against taxing capital gains more heavily: (i) it would discourage socially beneficial activities, such as innovation, (ii) implementing structural changes is unadministrable, and (iii) the ‘lock-in’ effect means that increasing the tax rate is an inefficient way to raise revenue. To address concerns with the unpopularity of taxing unrealized gains during one’s lifetime and retroactive taxes, we conclude with a partial proposal for constructive realization at death that would apply only to gains accrued after a certain date, while allowing for discounted pre-payments of tax liability.