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Wikipedia said:
[Humberto Delgado's] passage as a Military Attaché and Aeronautic Attaché to the Portuguese Embassy in Washington, D.C. in 1952 pushed him into the defence of democratic ideals, and inspired him to run as the democratic opposition's candidate for the Portuguese presidency in 1958.[5]

As incumbent president Craveiro Lopes had been coerced not to run to reelection by Salazar [because Craveiro Lopes was not content to be a puppet], Delgado faced naval minister and staunch conservative Américo Tomás in the 1958 presidential election. Delgado campaigned vigorously, even though he faced nearly impossible odds. In a famous interview on 10 May 1958, in the Chave d'Ouro café, when asked what would be his attitude towards Salazar, Delgado made one of the most famous quotations in Portuguese politics: "Obviamente, demito-o!" ("Obviously, I'll sack him!"). He was well aware that the president's power to remove the prime minister from office was essentially the only check on Salazar's power.

His outspoken attitude earned him the epithet of "General sem Medo" ("Fearless General" or literally "General without fear"). Nevertheless, Delgado was ultimately credited with only around 25% of the votes, with 75% in favor of Tomás.[6] Most neutral observers believed that Delgado would have won had the election been conducted honestly, and that he only lost due to massive ballot-box stuffing for Tomás by the PIDE. Nonetheless, Salazar was worried enough that he transferred election of the president to the legislature, which was firmly controlled by the regime.

Obviously Salazar would never allow a free and fair vote, though Delgado's strong support IOTL scared the shit out of him. Let's say Salazar slips in the bathtub a bit earlier than OTL, and President Craveiro Lopes (who would later go on to support a coup attempt against Salazar in 1961) takes advantage of his resulting incapacity to nix the ballot stuffing attempts. Delgado wins. What next? Will he be able to democratize Portugal? What would be his positions towards the Portuguese colonies and Europe (especially Franco)?
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