While the Kadi affair has attracted a lot of attention, this Article approaches it from a rarely used contextual theoretical perspective of resolving institutional conflicts through reflexive sincere cooperation. The argument is short and simple: The institutional relationship between the EU judiciary and the UN Security Council should have been conducted not in strategic-pragmatic terms motivated by institutional power-plays, but rather by genuine pluralist institutional cooperation. The argument is preceded by an in-depth analysis of the theoretical and concrete practical shortcomings stemming from the lack of institutional cooperation between the UN and the EU in the Kadi affair. These shortcomings were not inevitable, as the EU and the UN legal and political systems are already connected with a whole set of bridging mechanisms. These should be, however, strengthened and their use should be made more common. In order to achieve that, the Article suggests an amendment to the Statute of the Court of Justice of the EU and further improvement of the safeguards in the UN Security Council sanctioning mechanisms procedures. There is no dilemma: Enhanced institutional cooperation between the institutions of the two systems will work to their mutual advantage as well as, most importantly, maintain the rights and liberties of individuals like Kadi.