American law requires an insurable interest—a pecuniary or affective stake in the subject of an insurance policy—as a predicate to properly obtaining insurance. In theory, the rule prevents both wagering on individual lives and moral hazard. In practice, the doctrine is avoided by complex insurance transaction structuring to effectuate both origination and transfers of insurance by individuals without an insurable interest. This paper argues that it is time to abandon the insurable interest doctrine. As both the English and Australian experiences indicate, elimination of the insurable interest doctrine will have little detrimental pecuniary effect on the insurance industry, while freeing consumers considerably. Indeed, New York comes to the brink of eliminating the doctrine in its recent decision in Kramer v. Phoenix Life Insurance Co. by sanctioning an immediate life insurance assignment procedure that in effect eliminates the need for an insurable interest in the assignee. However, Delaware, in PHL Variable Insurance Co. v. Price Dawe 2006 Insurance Trust and Lincoln National Life Insurance Co. v. Joseph Schlanger 2006 Insurance Trust, breathes new life into an old doctrine. Overall, though, adhering to an arcane doctrine that prevents the value of an insurance policy from being realized without extreme legal burden both hampers the market and harms consumers, as the benefits of such transactions are both lessened by transaction costs and accrue to only a select few individuals.