Optimal Parlay Wagering and Whitrow Asymptotics: A State-Price and Implicit-Cash Treatment

Abstract: For independent multi-outcome events under multiplicative parlay pricing, we give a short exact proof of the optimal Kelly strategy using the implicit-cash viewpoint. The proof is entirely eventwise. One first solves each event in isolation. The full simultaneous optimizer over the entire menu of singles, doubles, triples, and higher parlays is then obtained by taking the outer product of the one-event Kelly strategies. Equivalently, the optimal terminal wealth factorizes across events. This yields an immediate active-leg criterion: a parlay is active if and only if each of its legs is active in the corresponding one-event problem. The result recovers, in a more transparent state-price form, the log-utility equivalence between simultaneous multibetting and sequential Kelly betting. We then study what is lost when one forbids parlays and allows only singles. In a low-edge regime and on a fixed active support, the exact parlay optimizer supplies the natural reference point. The singles-only problem is a first-order truncation of the factorized wealth formula. A perturbative expansion shows that the growth-rate loss from forbidding parlays is $\OO(\eps^4)$, while the optimal singles stakes deviate from the isolated one-event Kelly stakes only at cubic order. This yields a clean explanation of Whitrow's empirical near-proportionality phenomenon: the simultaneous singles-only optimizer is obtained from the isolated eventwise optimizer by an event-specific cubic shrinkage, so the portfolios agree through second order and differ only by a small blockwise drag.