Election speeches play an integral role in communicating the vision and mission of the candidates. From lofty promises to mud-slinging, the electoral candidate accounts for all. However, there remains an open question about what exactly wins over the voters. In this work, we used state-of-the-art natural language processing methods to study the speeches and sentiments of the Republican candidates and Democratic candidates fighting for the 2020 US Presidential election. Comparing the racial dichotomy of the United States, we analyze what led to the victory and defeat of the different candidates. We believe this work will inform the election campaigning strategy and provide a basis for communicating to diverse crowds.