From Betting to Empirical Bernstein LIL

Consider betting against a sequence of data in $[0,1]$, where one is allowed to make any bet that is fair if the data have a conditional mean $m_0 \in (0,1)$. Cover's universal portfolio algorithm delivers a worst-case regret of $O(\ln n)$ compared to the best constant bet in hindsight, and this bound is unimprovable against adversarially generated data. In this work, we present a novel mixture betting strategy that combines insights from Robbins and Cover, and exhibits a different behavior: it eventually produces a regret of $O(\ln \ln n)$ on almost all paths (a measure-one set of paths if each conditional mean equals $m_0$ and intrinsic variance increases to $\infty$), but has an $O(\log n)$ regret on the complement (a measure zero set of paths). Our paper appears to be the first to point out the value in hedging two very different strategies to achieve a best-of-both-worlds adaptivity to stochastic data and protection against adversarial data. We contrast our results to those in Agrawal and Ramdas [2026] for a sub-Gaussian mixture on unbounded data: their worst-case regret has to be unbounded, but a similar hedging delivers both an optimal betting growth-rate and an almost sure $\ln\ln n$ regret on stochastic data. Finally, our strategy witnesses a sharp game-theoretic upper law of the iterated logarithm, analogous to Shafer and Vovk [2005].

Betting-based sequential tests and Blackwell approachability are linked by a rate-explicit reduction through support-function residuals. For a compact convex target $S$ and vector observations $r_t$, an OCO learner selects a predictable normal $w_t$ and produces $q_t=\langle w_t,r_t\rangle-h_S(w_t)$. We prove the exact pathwise identity $\dist(\bar r_T,S) =\frac1T\sum_{t=1}^Tq_t+\frac{\Reg_T}{T}.$ When $|q_t|\leq B$, composing this identity with one-sided betting yields a finite-time transfer: if the OCO and log-wealth regrets are at most $a_T$ and $\ell_T$, respectively, then a target gap exceeding $$\frac{a_T}{T} +2B\sqrt{\frac{\log(1/α)+\ell_T}{T}}$$ forces rejection by time $T$, while non-rejection certifies the converse radius. We then formulate a controlled stochastic experiment in which an action selected after $w_t$ satisfies Blackwell's supporting-halfspace condition for every null mean payoff. The resulting wealth is an e-process under adaptive nulls; sublinear OCO regret gives stochastic approachability, whereas persistent mean separation under an alternative gives exponential wealth at rate at least $δ^2/(4B^2)$. Deterministic Blackwell games and passive tests are, respectively, the noise-free and singleton-action cases of this protocol. Bounded two-sample means, kernel MMD, and active heterogeneous data sources instantiate the reduction. The resulting connection is exact algebraically, quantitative at finite time, and operational when experiments are controlled.

Language models are saturating benchmarks for procedural tasks with narrow objectives. But they are increasingly being deployed in long-horizon, non-stationary environments with open-ended goals. In this paper we introduce KellyBench, an environment for evaluating sequential decision-making in sports betting markets. Agents are placed in a sequential simulation of the 2023-24 English Premier League season and tasked with maximising their long-term bankroll growth. They are given detailed historical data, including advanced statistics, lineups, and public odds. To succeed they must build machine learning models, identify edge in public markets, and adapt as the environment changes over time. We find that all frontier models evaluated lose money on average over the course of the season for five seeds. The best performing model achieves an average return of -8%, and many models experiencing ruin across seeds. To judge strategy sophistication, we use a human expert rubric to grade each model and find their approaches to be unsophisticated compared to human baselines; Claude Opus 4.6 achieves a rubric score of 26.5%, which means there is significant room for improvement. KellyBench is available as an open-access API endpoint at https://openreward.ai/GeneralReasoning/KellyBench.