Chapter 1 shows that there is a negative relationship observed between sanctions and civil liberties in the target country, which is driven by how exposed the target country's trade was to the sanctioning countries. Using a fixed panel regression covering 160 countries from 1972-2005, it is found that import exposure to the sanctioning countries drives this negative relationship, with every percentage point of import exposure reducing the inverted FHI freedom score by 0.165 points. This implies that restricting imports to a country that promotes an oppressive response by the targeted government. Chapter 2 examines whether countries change their trade patterns in response to economic sanction threats in addition to imposed sanctions. Using a bilateral gravity panel dataset covering 180 countries from 1950-2005 I find that imposed sanctions cause a very significant 55.43% increase in purchases from third party suppliers or a smaller 49.78% increase in sales to third party buyers during sanction events. Sanction threats cause a 42.05% increase in purchases from third party suppliers, and a 42.76% increase in sales to third party buyers, all significant at the 1% level. I conclude that both imposed sanctions and sanction threats lead to a significant increase in trade with third party countries, preempting and subverting sanction regimes. Chapter 3 studies whether there is evidence of cheating during sanction events by examining the difference in reporting for exports in the selling country versus imports in the buying country. A systematic change in reporting behavior is detected, with the log difference of reported exports minus reported imports increasing 7.46% in the case of exporter imposed sanctions, and decreasing 9.86% in the case importer imposed sanctions. This is consistent with the theory that firms in the sanctioning countries face harsher penalties for being caught compared to the targeted countries.