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This paper examines “smart sanctions” as statecraft by presenting a new theoretical foundation to understand how target states manage to overcome them by turning sanctions into an opportunity. The paper presents a case study on sanctions targeting the Russian oil (crude oil and petroleum products) exports since Russia’s invasion of Ukraine. The paper examines in detail how Putin’s Russia has leveraged opportunities for rent-seeking throughout the oil value chain, attracting a large set of collaborators in the Global South, including Central Asia, and beyond. This approach has transformed key players (government and corporates) in a wide geography into collaborators for circumventing sanctions on Russian oil. The paper’s focus on Putin’s Russia presents a highly policy relevant research with the potential to enrich understanding pathways for augmenting the effectiveness of sanctions.