This paper seeks to address the question, “How do women negotiate international crisis and what are their outcomes?” To do this, I derive hypothesis from both the realist and feminist theories to test in three case studies of prominent women leaders in the 20th-21st centuries. I analyze qualitative case studies on Margaret Thatcher, Dilma Rousseff, and Angela Merkel, in which I test variation in negotiation style affecting outcomes. In addition to assessing their early influences and overall negotiating styles, I look at the specific cases of The Falkland Islands Crisis, the NSA Surveillance Crisis, and the Ukraine Crisis negotiations. I find that Merkel and Rousseff embraced collaborative approaches, while Thatcher consistently used a confrontational approach. I also find that collaborative approaches tend to result in better outcomes for all parties, while a confrontational approach creates winners and losers. Overall, this offers more support for feminist theory than realist theory