This article begins with a brief discussion of the background of the USSR/Russia rapprochement with the General Agreement on Tariffs and Trade/World Trade Organization (GATT/WTO) and some of the acute problems of the negotiation process. It is argued that the Russian Federation has received acceptable, balanced conditions of membership. The advantages gained during the first years of WTO membership are listed, both for the national economy and in the foreign arena. However, it is shown that, 10 years later, the benefits of membership are significantly lower in comparison with initial projections. This gap is attributed to the state of the Russian economy and the extinction of the continuing economic model based on the extraction and export of raw materials. The Russian economy needs real structural reforms and modernization, which would change the structure of exports in favour of finished products and modern services. Only in this case can the benefits of WTO membership increase significantly, justifying the original forecast. The article concludes with a discussion of current challenges in the world economy and trade, the crisis experienced by the WTO, and the active position of the Russian Federation on the future reform of the WTO.