@idonotlikeusernames you keep on insisting in giving me work, hum? Just kidding, bro, glad to help however I can, even if I am living through a chronic lack of time kind of period.
Yep, pretty much. Imagine this… Instead of Colombo (probably Portuguese, there is plenty proof of it) offering his services to the Kings of Spain (was it a plot by the Portuguese crown? A consequence of portuguese crown’s insistence that the path to India was through the cape of good hope?) he persuaded the Portuguese Crown to give him the resources to organize an expedition towards West… And Portugal has now an island in the Caribbean!
After that, you could make history evolve at its normal course. Portugal understood that America wasn’t India and continued with its normal pathway to India, with Vasco da Gama finally finding a way in the last years of the XV century. So, the treaty of Tordesillas was signed as in the “real” history, with the small difference of Portugal receiving the right to keep the Island already occupied by it. Heck, you might even get creative and put it as a trade for the Canary Islands. Spain got Canary Islands and Portugal got the Island you want to write about.
Yeah, I can try to help out if needed with the Cold War and the Portuguese colonial issues, Salazar and fascism. Gald to help.
And besides, our colonial history is slightly different from most countries’ colonial history (every country’s colonial history is different, obviously). The island, if populated by natives before Portuguese presence, would certainly keep them during and after our presence there. Spanish went on to conquer their territories, we were traders that ended up colonizing the places, mostly for its resources and wealth.
Please note that I haven’t checked what your idea is about, so my input is being delivered in a very improvisational manner. Do you want the island to be part of the Portuguese Empire at that time? Fully independent? Some form of autonomy?
The different scenarios would give you different things to work with. If you have it independent, you can work it however you want, it’s just a difference in culture and history, with a bigger presence of native peoples, and a traditionally less interventionist empire, even if with the “State” or the “Crown” traditionally holding a big chunk of power and an intimate relationship with the established elites and businesses.
If it is fully integrated in the Empire, not suffering from the wave of independences that shook the Americans during the XIX century, you would have the opportunity to deal with the presence of a pro-independence movement in place long before the start of the Colonial Wars. And you would have fascism and the special kind of capitalism Salazar and the Estado Novo promoted.
If you want it to be autonomous, you could get the best of both worlds, with a Fascist government and its imperialist and unity dreams crushing the past autonomy of the region, especially after the start of the Colonial Wars elsewhere, and a bigger degree of customization of the Island’s structures, elites and traditions.
Just some ideas
Btw, you could even put it right after the Carnation Revolution, with the US invasion of the place or theirs plans to do it because of the “scary communists” taking over the country, nationalizing part of the economy in order to destroy the regime’s bastion of power, giving freedom to the colonies and so on. Heck, the US had plans to invade Portugal after the Carnation Revolution, and another parallel plan of taking over Azores and declare its independence (because of the military base they have there since WW2 or something like that), there are records of conversations of the US’s executive and military branches with Kissinger saying so. Fun stuff.