First, we have to acknowledge that there is very little difference between a master politician and a duplicitous trickster. Much of politics involves actions that are at least somewhat questionable.
Second, we have to also acknowledge that our modern standards are different from those of the early 1900s. Today, Roosevelt’s actions would be seen as duplicitous and bullying. Public opinion would likely condemn a president who took similar actions. In this sense, we can say he was duplicitous.
However, by the standards of the time, he was more of a master politician. This was the era of imperialism. There was little disapproval of those sorts of actions, particularly towards a country of people who would have been seen as inferior to Americans. In that sense, we can say he was a master politician because he got what his country wanted.