We begin by showing that every theory of the value of uncertain prospects must have one of three unpalatable properties. _Reckless_ theories recommend giving up a sure thing, no matter how good, for an arbitrarily tiny chance of enormous gain; _timid_ theories permit passing up an arbitrarily large potential gain to prevent a tiny increase in risk; _non-transitive_ theories deny the principle that, if A is better than B and B is better than C, then A must be better than (...) C. Having set up this trilemma, we study its horns. Non-transitivity has been much discussed; we focus on drawing out the costs and benefits of recklessness and timidity when it comes to axiology, decision theory, and normative uncertainty. (shrink)