When Adam Smith – author of Wealth of Nations (1776) and Theory of Moral Sentiments (1759) – was elected a professor at the University of Glasgow in 1751, he also joined an annuity ‘scheme’ that was unique for its time. The Scottish Ministers’ Widows’ Fund, as it was known, offered members of the Presbyterian Church as well as the university a choice of levels at which to contribute investment savings, ranging from 2 to 10 percent of their wages. The life-contingent benefits were in the form of a reversionary annuity to a spouse and/or lump sum death benefit to children. This article (i) describes the scheme in financial and actuarial terms, (ii) values Smith's reversionary annuity and (iii) examines the choices made by individual participants. The specific research contribution is to compile the archival data to measure the extent of insurance anti-selection and to demonstrate that debates around choice architecture, default options and auto-enrollment, which infuse the literature in the twenty-first century, were prevalent in the mid eighteenth. For the record, Adam Smith actively contributed at the highest allowed rate, but it wasn't a ‘good’ investment for him, either ex ante or ex post. As for why, one must read the article.