In the summer of 2014, Russia forcibly annexed Crimea from Ukraine and then actively supported ethnic Russian separatists in an on-going irredentist bid in Eastern Ukraine. This aggressive policy threatens to challenge NATO and the United States in its support of Ukraine and other nations of Eastern Europe. From this changing strategic environment, three central questions emerge: (1) What is the Russian strategy in their periphery? (2) What is the appropriate U.S. response? (3) What are the implications for U.S. landpower? Vladimir Putin’s grand strategy relies on a complex mix of diplomatic, informational, military, and economic factors to preserve and expand Russian global power. Putin’s strategy hinges on maintaining internal legitimacy, advancing a narrative of Russian greatness, manipulating nationalism, and protecting sources of revenue. He seizes opportunities to improve his position by controlling the media and the wealth of the elite class. Additionally, he maintains government control of large sectors of the Russian economy and industry, while engaging in energy politics abroad to advance its national interests. Finally, Putin is determined to keep former Soviet bloc countries oriented politically and economically toward Russia. In this, he espouses distinctly anti-Western rhetoric, casting NATO and the United States as Russian adversaries. Putin wields substantial control over the entire Russian system, and he will not willingly give up power. His governing style is called “competitive authoritarianism,” which is a blend of old Soviet style leadership laced with hints of democracy. Yet, in this, he must maintain popular support, energy revenues, a strong military, and an elite that will not challenge his position. Adding to his woes, Putin’s aggressive tone against the West gives him less and less room to maneuver diplomatically. Yet, he will continue to propagate a nationalist agenda, while bashing the West and blaming America for Russia’s hardships. It seems, that at least domestically, his gambit is working. In the wake of the crises in Crimea and the Ukraine, Putin’s popularity has reached impressive heights. Yet, not all is going well for him as there are dark economic predictions on the horizon for Russia. Western sanctions indeed have taken a toll, but they are only partly responsible for the economic crisis Putin now faces. Other factors include Russia’s energy-dependent market, a “corrupt-and-control” economy based on patronage and fraud, the collapse of the ruble, and declining oil prices. To compound matters for Moscow is the inclination of some European customers, not wanting to be subject to potential economic blackmail, and thereby seek non-Russian alternatives to their energy needs.