IDK TR was a monster that would have made Echidna proud to call her own he might have done it but that requires a whole other kettle of fish as it wouldn't be happening during any recognizable Spanish American war. In any real sense it seems ASB to me for the US to get the Canaries and hold them. The only way this might even seem possible is if one or more other European powers were backing them and they expelled most of the population off the island.snip
I mean if the US wanted territory so bad it tried to keep the Canaries that it wouldn't have listened to Spain on conditions for Cuban independence.