Abstract: China has traditionally been regarded as a continental power. However, the 21st Century Maritime Silk Road (MSR), launched in 2013, shapes China’s intention to become a global maritime power. The initiative is the most significant contribution to increasing global maritime connectivity in recent decades. The volume and impact of Chinese investments in Europe’s seaports are remarkable. This article proposes a fundamental framework to assess who benefits from the initiative. Since quantitative cost-benefit analyses (CBA) hardly apply to multifaceted and partially unquantifiable phenomena, we suggest assessing the MSR by means of a comprehensive qualitative CBA. We opted for a qualitative CBA due to ontological and epistemological reasons: on the one hand, the complex and multilayered nature of the problem is difficult to monetize, and, on the other hand, our argument is not final, as it attempts to assess a given policy before its implementation is sufficiently mature. In this vein, we apply the problem-solving methodology ‘analytic hierarchy process’. While the media have disproportionately stressed the negative effects of the MSR, we conclude under this framework that (i) for China, MSR benefits largely outweigh associated costs; (ii) for participating countries, MSR benefits outweigh the associated costs only after cost-mitigating measures are incorporated; and (iii) for non-participating countries, MSR costs outweigh associated benefits.