At the age of twenty-four, in 1952, Enrique established a company called 'Industrial Agricultural Services of Masaya' (SAIMSA), which eventually became one of the leading producers of cotton in Central America.
In the 1980s, the successful businessman openly condemned Nicaraguan guerrilla leader and President Daniel Ortega, who was known for his restriction of media and association with Venezuelan President Hugo Chávez. Bolaños was arrested on three occasions, while his company 'SAIMSA' was seized and handed-over to small farmers.
From 1983-88 he acted as the President of the 'Supreme Council for Private Enterprise' ('COSEP'), which aimed at reducing government control on private enterprises.
In 1990, when the presidential elections were held, Bolaños decided to run as a candidate. However, his party, the ‘National Opposition Union', chose his colleague Violeta Chamorro instead, stating that the former was too obstinate to work with.
Six years later, Arnoldo Alemán, a member of the 'Liberal Constitutionalist Party', and a candidate for the presidential elections, decided to appoint Bolaños as his campaigner. Alemán won the elections against President Ortega, and Enrique was elected Vice-President in 1997.
In 1998, hurricane ‘Mitch', caused heavy rainfall in Nicaragua, Guatemala and Honduras, resulting in floods that killed thousands of people and destroying millions of homes. During this catastrophe, it was the Vice-President who took charge of foreign aid and worked on the country's laws that dealt with avoiding natural disasters.
The Nicaraguan politician contested the elections in 2001, under the wing of the 'Liberal Constitutionalist Party', being recommended by former president Arnoldo Alemán. During the campaign, citizens did not show much confidence in Bolaños, owing to defamation tactics by rival Ortega, and also his association with his corrupted predecessor Arnoldo.
In August the same year, the presidential candidate openly criticized fraudulence in the government, but avoided confronting Alemán. He also accused the leftist Ortego of draining the country of its wealth. The elections were won by Enrique, with a majority of 56.3% votes.
The President's term began on January 10, 2002, and within two days, he started taking legal action against all those, former and present, office holders in the government who had indulged in fraudulent activities.
Enrique arrested his predecessor Alemán on corruption charges, and sentenced him to twenty years of imprisonment. As a result the former was made to leave the 'Liberal Constitutionalist Party' by his comrades. He then formed a new political party called 'Alliance for the Republic' ('APRE').
The President of Nicaragua signed the 'CAFTA', or the 'Central America Free Trade Agreement', along with the United States, Costa Rica, Honduras, El Salvador, and Guatemala, in 2005. The same year, he reduced the power held by the executive branch of the parliament, by limiting its control over the appointment of state officials.
Despite his attempts to fight corruption in the country, Bolaños has been condemned for his old association with Alemán, and the remuneration he received as Vice-President. Once he came into power, his salary was reduced substantially, and his pension was withdrawn.
The President aimed at minimizing foreign financial obligation with the help of the 'World Bank' and the 'International Monetary Fund'. Furthermore, he introduced measures like the 'National Development Plan' for poverty alleviation and promotion of agriculture.
In 2007, Enrique's term ended, and Daniel Ortega was once again elected President, after winning over Eduardo Montealegre, a candidate representing the party 'Nicaraguan Liberal Alliance'. The Liberal party collaborated with Bolaños' 'Alliance for the Republic' during the campaigning.
Even though he was entitled to a place in the National Assembly, the former President retired from politics forever, after his term ended. He is currently a ceremonial member of the prestigious organization called ‘International Raoul Wallenberg Foundation’. He has also written articles like ‘Cómo vamos’, ‘Nicaragua: 165 años de vida independiente’, ‘Memorándums de la presidencia’, and ‘Ideas para todos’, amongst others.