In this paper we compare the situation of Human Resource Development (HRD) in Portugal in 1924, 1974, and 2024; the three points in time are quite important because the first date is situated near the end of the First Republic that followed the Monarchy in 1910, the second date marks the end of the Dictatorship that governed the country until 1974 and 2024 marks 50 years of democracy; therefore we aim at comparing three regimes through HRD and its impacts in the society in economic and social terms. We base ourselves on the basic Human Capital Theory, applied in macroeconomic terms, with relation to National HRD and with some analysis relating HRD to economic development and economic integration. We use secondary data and previously published works to illustrate a three-step methodology related to (1) context, (2) investment and (3) outcomes. We conclude that three very different political contexts produced three completely different types of investment, which in turn generated three completely different outcomes.