On the basis of laws and bills suggested during more than fifty years an attempt was made to identify possibility of settling the Cuban-American conflict in the future. Major source for the study was the site of the US Congress that provides both the texts of laws, resolutions and bills and the results of voting on them. Besides there are transcripts of the speeches made by members of both houses. The analysis served to understand what exactly motivated and motivates now the supporters of softer policy toward Havana. Comparison between their motivation and degree of support of their point of views of each historical period showed which of domestic political factors has the strongest impact on the Washington’s policy toward the Island of Freedom. In this respect, a position of American business and farm lobby in 21st century is very interesting. The pragmatism, by which the agricultural companies of the USA wanting to boost their income from trade with Cuba are governed, has contributed to promoting and encouraging ideas of US-Cuba normalization of relations on Capitol Hill. However, those who oppose the US-Cuba rapprochement still occupy very strong position. They facilitate the intensification of conflict and further escalation of hostility. They actions are not motivated by economic pragmatism, but by another factors relating to the political games, not to mutual benefits. Between those conflicting viewpoints, there is the group of lawmakers who might be termed supporters of compromise. It is on this basis that there are the debates between the supporters and opponents of the normalization of the US-Cuba relations. Grace of this group of congressional representatives all of new acts that regulate policy toward Havana has become more moderate than in Cold War. The evolution of Congress bills initiated during more than 50 years may indicate a shift in the political situation in the US Congress.