Gambling regulation can be informed by various conceptual models, such as the public health model which views it as being intrinsically harmful like tobacco, and which therefore implies the use of population-based harm prevention measures. The children’s game of whack-a-mole has also been used to describe the challenges of online gambling regulation, where new regulatory issues continue to emerge. Here I explore the implications of seeing gambling regulation like the strategic gambling game of poker – a metaphor that is close to home, and which directs attention on the gambling industry’s ability to constantly innovate its products and practices. I argue that gambling policy should not just act on current products and practices, but also strategically consider potential harmful innovation. Using international examples, I show how gambling regulations have failed by stating key terms vaguely, by containing exploitable loopholes, and by giving gambling operators strategic flexibility in regulatory compliance more broadly. A more strategic regulatory approach is therefore recommended, which follows an expert poker player’s mindset by anticipating and countering potential gambling operator responses. This means defining key terms concretely, implementing broadly applicable policies, and restricting gambling operators to evidence-informed actions. Other implications of the model include minimizing operators’ informational advantages over regulators. Reductions in populations harms can only be achieved by recognizing the inherent mutability of gambling products and the industry’s utilization of technology. While the whack-a-mole metaphor sees these challenges as being insurmountable, I argue that better outcomes could be obtained by taking a strategic approach to gambling regulation.