In this speech, Roosevelt claims:
How much freedom and self-government did the US allow Cuba and the Philippines to have?
Was the US really getting nothing from the deal but the assurance that rivals would not occupy these newly-liberated islands?
On the side of Cuba this was mostly well-meaning propaganda. By March of 1901 the United States had passed the Platt Amendment within the 1901 Appropriations Bill.
Cuba’s constitution had been adopted in February 1901 by Cuban delegates to the constitutional convention, but the United States did not agree to ratify it until June of 1901 after it had been amended to fold in the demands of the Platt Amendment.
The preamble is telling:
Preamble: For the recognition of the independence of the people of Cuba, demanding that the Government of Spain relinquish its authority and government in the island of Cuba, and withdraw its land and naval forces from Cuba and Cuban waters, and directing the President of the United States to use the land and naval forces of the United States to carry these resolutions into effect, the President is hereby authorized to "leave the government and control of the island of Cuba to its people" so soon as a government shall have been established in said island under a constitution which, either as a part thereof or in an ordinance appended thereto, shall define the future relations of the United States with Cuba.
The US was the one that would unilaterally decide whether to withdraw US troops and allow Cuba to self-govern. Some more troubling parts:
III. That the government of Cuba consents that the United States may exercise the right to intervene for the preservation of Cuban independence, the maintenance of a government adequate for the protection of life, property, and individual liberty, and for discharging the obligations with respect to Cuba imposed by the treaty of Paris on the United States, now to be assumed and undertaken by the government of Cuba.
IV. That all Acts of the United States in Cuba during its military occupancy thereof are ratified and validated, and all lawful rights acquired thereunder shall be maintained and protected.
VII. That to enable the United States to maintain the independence of Cuba, and to protect the people thereof, as well as for its own defense, the government of Cuba will sell or lease to the United States lands necessary for coaling or naval stations at certain specified points to be agreed upon with the President of the United States.
VIII. That by way of further assurance the government of Cuba will embody the foregoing provisions in a permanent treaty with the United States.
Even still, Cuba was dependent on the US economy for sustenance, and the US returned in kind with a reciprocity agreement to aid Cuban sugar industry.
Looking forward into the future, the US took control over Cuba again in 1906.
Roosevelt of course knew about the Platt Amendment by this speech in November 1901.