as I understand it, the US went into the war with the idea of possibly gaining Cuba as a territory, and the Philippines were regarded (rather arrogantly) as a place that the US would 'civilize' and then set free. Somehow, it almost ended up the other way round, with the US fighting a really awful war against the Filipinos who objected to the idea, and Cuba becoming free from the start. I'd think the US trying to keep both places would have been a disaster, with intense guerrilla wars in both places, and the US military stretched to the breaking point...