It noted that the island's ties to Cuba and the province of Havana were so clearly established that the U.S. government must be considering "taking it only by purchase" because "It does not appear that it could be lawfully taken any other way.

... the rivers are numerous and several of them are navigable some miles inland; there are medicinal springs at Santa Fe–everything that could make the place desirable as a Winter resort seems there.

It is extremely rich in natural resources ... marble of exquisite quality ... mines of silver, quicksilver, and iron ... mahogany trees, including many of the male trees, which produce the class of wood from which furniture used to be made a hundred years ago, and which is now becoming very scarce ... Then there are cedar and various other woods, besides the immense growth of pines, from which the place takes its name, and the island also produces sulphur, turpentine, pitch and tar, tobacco, tortoise shell, and various other commodities.When the first Constitution of the Republic of Cuba was initially adopted on February 21, 1901, it did not mention the Isle of Pines as part of the nation's territory.

[3] After U.S. forces handed administration of the nation to the Cuban government on May 20, 1902, the Association of American Settlers on the Isle of Pines was quick to complain that they lacked government services and were "practically in a state of chaos as far as civil order is concerned",[4] though some in the U.S. did not take the complaint seriously, calling the Isle "a country which appears to exist at the present time solely for the purpose of supplying material for the comedian".

Ambassador in Cuba, signed treaties securing the U.S. right to lease lands at Guantanamo Bay and recognizing Cuban sovereignty over Isle of Pines.

[15] Senator William E. Borah argued that U.S. citizens–700 of the island's 4,250 residents were U.S. citizens–owned 90% of the land and had invested there in anticipation that Isle of Pines would enjoy a status similar to that of Puerto Rico.

[12] Senator Royal S. Copeland argued that Isle of Pines had strategic value and could serve as "a naval, military and air base of greatest importance to our protection of the [Panama] Canal".

[15] Cuban legislators argued that the original negotiations had recognized that the sovereignty of the Isle of Pines was part and parcel of the granting of the Guantanamo lease.

[22] In 1925 in Foreign Affairs, Benjamin H. Williams praised the ratification:[23] The relinquishment by the United States of its claim to the Isle of Pines may be regarded as but a minor territorial adjustment, but it carries more than ordinary significance because of its effect upon the intangible prestige of this country.