Roosevelt seemingly had little problem switching from campaign rhetoric to pragmatic statesmanship. Just one month after his inauguration, he dispatched Sumner Welles, a career diplomat, to intervene between Machado and his enemies. Before his departure to Havana, Welles issued a press release summarizing America's historical relationship to Cuba emphasizing the intervention of 1898, its geographic proximity, and the importance of island markets for American products. There was little question that Welles favored a continuation of American paternalism. The legal basis for inserting Welles into the conflict in Cuba was the same treaty and Cuban constitutional provisions that had been established to support American paternalism.
The State Department and their representative reasoned that the problems in Cuba were the direct result of Machado's arbitrary extension of his presidency and his use of terror squads to inflict reprisals on his opponents, real and perceived. They argued that the president in Cuba had schooled the islanders to believe that violence was the only method available to them to effect political change. If only Welles could convince Machado to work for a peaceful settlement through compromise, and protect American property and business interests, all would be well.
Like his predecessor, Harry Frank Guggenheim, Welles was deluded by his own expectations and Machado's dissembling. He believed the Cuban leader's assertions that he acting reasonably to unwarranted threats on his life and government. Even though he witnessed and reported one occasion when Machado's guards opened fire on a band of peaceful demonstrators, Welles remained convinced that Machado could maintain law and order. He didn't begin to doubt his own judgment until Machado repeatedly denied his recommendations.