If we assume that the parties involved in hypothetical insurance choice know that in the aftermath of their choice they will live in a market economy with private ownership and that the insurance against misfortune they are selecting will be implemented by general taxation of income and wealth and some form of redistribution, they will regard themselves as in effect gambling on their prospects. If they turn out to be winners in the market economy they will do better with a low tax rate for redistributive purposes, and if they are losers in the market economy they will do better with a higher tax rate and more redistribution. It is not clear why their preferences over this risk should fix what count as fair shares in the theory of distributive justice. Stipulating with Dworkin that the preferences of the average member of the community should be the determining preferences in this exercise does not clarify the issue.