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Wealthy Americans escape the income and estate taxes by holding assets at a legal remove. This general tax avoidance strategy—holding wealth “at a distance”—takes several forms, but the most powerful of all is the use of life insurance. Tax law has come to afford special treatment to life insurance due to some combination of reasoned policy, industry lobbying, and illogical application of existing tax rules and judicial anti-abuse doctrines. Courts have only recently begun to push back against taxpayers’ use of life insurance as a tax-free brokerage account, but the judicial crackdown is fatally flawed. This is because it rests on what I call “control doctrines,” or arguments that taxpayers should only become liable for paying taxes on their life insurance investments when they exercise direct, personal control over those investments. But I argue that taxpayers can benefit from such arrangements without exercising any control, and that economic benefit is a more appropriate basis for tax liability. I show that applying an economic benefit principle would produce simple, administrable rules superior to the control-based status quo in both the income tax and estate tax settings. My argument demonstrates that tax law must reject extreme legal formalism—such as the legal “distance” created through life insurance and trusts—in order to meet the challenge of high-wealth exceptionalism.