Sequential Probability Assignment with Contexts: Minimax Regret, Contextual Shtarkov Sums, and Contextual Normalized Maximum Likelihood

We study the fundamental problem of sequential probability assignment, also known as online learning with logarithmic loss, with respect to an arbitrary, possibly nonparametric hypothesis class. Our goal is to obtain a complexity measure for the hypothesis class that characterizes the minimax regret and to determine a general, minimax optimal algorithm. Notably, the sequential $\ell_{\infty}$ entropy, extensively studied in the literature (Rakhlin and Sridharan, 2015, Bilodeau et al., 2020, Wu et al., 2023), was shown to not characterize minimax regret in general. Inspired by the seminal work of Shtarkov (1987) and Rakhlin, Sridharan, and Tewari (2010), we introduce a novel complexity measure, the \emph{contextual Shtarkov sum}, corresponding to the Shtarkov sum after projection onto a multiary context tree, and show that the worst case log contextual Shtarkov sum equals the minimax regret. Using the contextual Shtarkov sum, we derive the minimax optimal strategy, dubbed \emph{contextual Normalized Maximum Likelihood} (cNML). Our results hold for sequential experts, beyond binary labels, which are settings rarely considered in prior work. To illustrate the utility of this characterization, we provide a short proof of a new regret upper bound in terms of sequential $\ell_{\infty}$ entropy, unifying and sharpening state-of-the-art bounds by Bilodeau et al. (2020) and Wu et al. (2023).