What made Saddam Hussein believe that he could get away with invading Kuwait?
How did he assess the political situation before Kuwait invasion?
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Saddam thought his foreign ministry asked the U.S. ambassador if it would be OK. The U.S. ambassador thought Iraq was just making a courtesy notification that Iraq would follow up on a dispute with Kuwait about oil drilling practices, so she said something non-committal. Iraq interpreted this as permission to conquer Kuwait.
Historically, when a major power says something non-committal in response to a second power saying it wants to invade a third country, the second power has often correctly interpreted the non-committal response as either "Go ahead", or "We'd rather you didn't, but we won't do anything serious if you do." For example: