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This chapter concentrates on Ukraine, but it also serves as the “scene-setter,” by providing much of the early history of the Soviet Union as it pertains to the nations on its periphery. It also describes Lenin’s theories on nationalities, and how those theories evolved over the years. The role of Ukraine in World War II is discussed, and the promises that Russia made after achieving independence. A discussion ensues on one of the principle strategic interests of Russia; namely, Ukraine’s role as an energy transit state. The chapter then turns to the events of modern times: Ukraine’s efforts to change allegiances from the East to the West, and the disastrous results of those efforts.