Simonsen's most far-reaching work was História Econômica do Brasil (1500-1822) [Economic History of Brazil (1500-1822)] written as a result of the author's teaching activities, which took place in 1936 as part of the course of Economic History of Brazil part of the Bachelor's Degree in Political and Social Sciences at the Escola Livre de Sociologia e Política de São Paulo [Free School of Sociology and Politics of São Paulo] (ELSP). The ELSP, an institution created in 1933 in the wake of the Constitutionalist Movement, with the mission of qualifying São Paulo's elite in "affairs of State", had Simonsen as one of its most important founders. História Econômica do Brasil stands as one of the most prominent essays on the understanding of the country, aligning with the contemporary trend of attempting to develop an understanding of Brazil that could shed light on the obstacles to modernisation and the historical roots of its backwardness. Like other authors of his generation, Simonsen found the origins of the problems to be overcome in colonial history. However, unlike many of his contemporaries, he understood that the specificity of Brazil's economic evolution was that of a colony geared towards developing capitalist dynamics, since it was already possible to observe the mercantile concern for profit since the arrival of the first Europeans on the American continent. Simonsen aligned himself with the thesis that the Portuguese monarchy established a strong central government organisation from an early stage. At the beginning of its history, Portuguese sovereigns were able to secure the largest sums of land and wealth for the Crown, but the Portuguese agrarian monarchy did not prevail. The expansionist tendency by sea seemed to be the only viable solution for the small kingdom, squeezed between the sea and the territories that would later form Spain. Although he acknowledged that maritime trade had existed since the late 13th century, with fishing, as Lúcio de Azevedo would describe it, being the first nautical school, it was only after the victory of the Master of Avis and the founding of the Sagres School that the Portuguese expansionist drive began to take more concrete form. This policy was not the result of a need to migrate, but of a government plan that aimed to conquer wealth, expand the faith and satisfy an increasingly restless and turbulent nobility. The Portuguese pioneering spirit in nautical matters is emphasised by the author as an extraordinary service rendered by Portugal to the world. However, like Spain, Portugal would profit little from the riches conquered by maritime expansion, as they suffered, among other factors, from competition from much more organised and active countries such as England, Holland and France.

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