His first political steps were inspired by his eagerness to implement his representative regime and democracy in the country. However, the internal power struggle which commenced and later ended in disaster, in 1817, made him change his approach. When he took control in 1817 he was convinced that the country needed adequate preparation to be able to promptly enjoy their newfound freedoms; that an initial period of education was necessary and that the way to channel this was by means of a military dictatorship, introduced by the ruling powers. 

He rejected the idea of establishing a monarchy in Chile. The aforementioned regime which implicitly resembled despotism, was on the other hand believed by San Martín to be the best type of dam to repress the anarchist overflows. He was of the opinion that the American people lacked the necessary level of culture which was required for adequate implementation of republican and democratic ideals. After all, they have been governed peacefully by a monarchy for centuries and he was afraid that a dramatic change of institutions would create serious consequences. In his opinion, the important thing to do was to insure Chile’s Independence and bring an end to absolutism. A European prince, who counted on the support of England as a guarantor of Chile’s emancipation, who governed the country under a constitutional system, capable of channeling its powers legally, was in San Martín`s opinion, a pledge for freedom and political order. 

He expressed these beliefs shortly after the battle of Chacabuco to the British Commodore Williams Bowles, who was travelling along the Pacific coast. He tried to infiltrate these in 1818 into the instructions given to Antonio José de Irisarrí, Chile’s European diplomatic agent but O'Higgins brought a stop to his attempt just in time. In 1822, when San Martín sent Juan García del Río and Diego Paroissien from Peru to the Old World, with the task of obtaining support for a new Monarchical Project, once again his plans were brought to a halt. 

O'Higgins’ attachment to his own, personal dictatorship, as the best system for the country, led him to oppose another type of influence.  The influence that the Northamerican agents Williams Worthinton and Theodorick Bland were exerting, trying to persuade him to adopt their own country’s political system: a representative democracy, federalism and religious freedom. However, although O'Higgins rejected these institutions as premature or inadequate, he was forced to, albeit briefly, establish at least the appearance of a constitutional regime, with certain limitations on his power, in order to satisfy the pressure due to public opinion.