The article deals with the evolution of insurance in the Russian Federation in 1998-2012 through the prisms of statistical and political economy approach. Insurance is viewed as the vital indicator of the level of capitalism. The latter is justified both by theoretical insights and short historical analysis of insurance. The quantitative and qualitative success of insurance in the Russian Federation compared to 1990-s are demonstrated. However, comparison with other countries, particularly with the USA, reveals its extremely low level of development. The author also considers insurance in prerevolutionary Russia and USSR. Insufficiently successful efforts of several successful (in other areas) entrepreneurs to modernize the Russian insurance are analyzed. The low level of the Russian insurance explains the extremely low level of capitalism in Russia, the author concludes.