In this article, we test the theory of “The Coalition of the Opting” by counterfactually including a paragraph in the Yalta Charter, regulating the security cooperation between Georgia, Ukraine, Azerbaijan, and Moldova, welcoming them to develop both call and put options between the member states. The counterfactual Charter is applied to three examples of Russian armed aggression: the war on Georgia in 2008, the war on Ukraine in 2014, and the full-scale invasion on Ukraine in 2022. Although the application of the counterfactually designed options most likely would not have altered the outcome of these aggressions, our findings suggest that the very existence of a coalition of the opting nevertheless could have compelled Russia to think twice before attacking. Arguably, the additional time could have enabled both the coalition and the Western community to undertake counteractions that factually now were absent.