Winner's Curse Drives False Promises in Data-Driven Decisions

Data-driven optimization aims to translate a machine learning model into decision-making by optimizing decisions on estimated costs. Such a pipeline can be conducted by fitting a distributional model which is then plugged into the target optimization problem. While this fitting can utilize traditional methods such as maximum likelihood, a more recent approach uses estimation-optimization integration that minimizes decision error instead of estimation error. Although intuitive, the statistical benefit of the latter approach is not well understood yet is important to guide the prescriptive usage of machine learning. In this paper, we dissect the performance comparisons between these approaches in terms of the amount of model misspecification. In particular, we show how the integrated approach offers a ``universal double benefit'' on the top two dominating terms of regret when the underlying model is misspecified, while the traditional approach can be advantageous when the model is nearly well-specified. Our comparison is powered by finite-sample tail regret bounds that are derived via new higher-order expansions of regrets and the leveraging of a recent Berry-Esseen theorem.

Previous research has investigated the potential of refugee matching for boosting refugee outcomes, first considered by Bansak et al. (2018). This paper demonstrates the stability of counterfactual impact evaluation results in the context of refugee matching in the United States using a range of off-policy evaluation methods. In order to estimate counterfactual impact and test the robustness of our results, we employ several evaluation methods, including inverse probability weighting (IPW) and multiple variants of augmented inverse probability weighting (AIPW). We also consider various modifications, including alternative modeling architectures and different assignment procedures. The impact estimates remain consistent in magnitude in all scenarios as well as statistically significant in most cases. Furthermore, the estimates are also consistent with the results originally presented in Bansak et al. (2018).

Organizations often have an incumbent predictive model in production when new data sources become available. Because historical training data lack the new features, a challenger model must be trained on a small but growing full-feature dataset. We study whether, and when, the organization should switch to the challenger. The decision is statistical and economic: the challenger's predictive performance improves as full-feature data accumulate, but repeated retraining is costly and delays benefits from deployment. We develop a framework linking learning-curve dynamics to model-switching economics. Under a standard power-law learning curve and finite data-collection horizon $T$, the optimal time to train and evaluate the challenger scales as $T^{1/(1+α)}$: learning-curve shape (through its learning speed $α$) is the primary theoretical determinant of when to stop experimenting; costs determine switching profitability. Even without knowing the learning curve, the operational problem is tractable: we show that any algorithm stopping on the $T^{2/3}$ scale and making reliable switch/discard decisions achieves $O(T^{2/3}\sqrt{\log T})$ regret relative to a full-foresight oracle. We propose a sequential evaluation algorithm that uses local learning-curve trends to anticipate improvement, and test it in a real-world credit-scoring study. Even with this local approximation, the algorithm theoretically and empirically achieves near-oracle performance. It is also more stable than greedy sequential evaluation algorithms, where noisy early estimates trigger premature discarding, or simple one-shot evaluation algorithms, which work only when their fixed evaluation time matches the (unknown in practice) theoretical timing scale. Our framework offers a step toward principled model governance when new data sources require costly collection, validation, and deployment.