The Russo-Ukrainian War provides a unique, somewhat fortuitous, and data-rich opportunity to compare competing proxy war strategies. On one side resides Russian proxy war strategy, and on the other, the American strategy. Each strategy is quite unique from the other. Yet, in the rich, and often sad, irony that accompanies war, each state’s proxy strategy feeds off the other, having transformed the conflict into a grinding war of attrition. In comparing Russian and American proxy strategies in Ukraine, one quickly finds that the traditional conceptual standards of proxy war scholarship, such as plausible deniability and indirectness, are no longer salient considerations for great power proxy war. Things such as pervasive overhead surveillance and reconnaissance tools, social media, globally accessible mass communication, and open-source reporting have all but rendered those ideas obsolete features of a bygone era. In comparing Russian and American proxy strategies, one finds great powers today use proxy strategies because they render significant benefits in temporal advantage and strategic flexibility. Russia’s reliance on the Donetsk and Luhansk People’s Armies and the Wagner Group provide it time and flexibility it wouldn’t otherwise have using its own forces. Additionally, the American strategy – providing weapons, intelligence, training, and money to Ukraine – to defeat Moscow on Ukrainian battlefields, likewise provides Washington’s policymakers time and flexibility that they wouldn’t have if utilizing American forces. In the end, comparing great power proxy strategies in Ukraine provides an excellent opportunity for scholars, policymakers, and practitioners alike to update their understanding of proxy war studies.