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We analyze the driving forces behind China’s New Silk Road (NSR) initiative and find that they not only included short-term factors, such as the US “rebalance” of forces in Asia and China’s economic slowdown since 2012, but also long-term factors such as China’s ambition to recover its past glory and integrate itself still further into the global economy. We then look at the external challenges facing China’s initiative, such as geopolitical competition, fear of overdependence, and political instabilities along the old silk routes. We highlight China’s policy dilemmas and discuss the sustainability of China’s NSR initiative and its implications for the world. Our conclusion is that China’s initiative could be in for a rocky road, but if it strikes a good balance between its diplomatic objectives and means and its values and actions, the NSR could speed up regional integration.