You can use the US embargo on Cuba as a case study -- see this video: https://www.youtube.com/watch?v=CJETjgJM-Q4. The conclusion is roughly that the sanctions did not work, they only strengthened Cuba's relationship with the Soviet Union, as well as serving to unite the citizens of Cuba against a common enemy and thus consolidating support for Fidel Castro. Another comment makes the same point about Iran and China today
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