The island territories and democracy

Left to right: Flags of Puerto Rico, Guam, Northern Mariana Islands, American Samoa, and U.S. Virgin Islands. (Images from 1,2,3,4,5.)
To give an idea of the relative scale of the island territories, here they are together. Some small islands omitted. (Image built from 1,2,3,4.)

Statehood

Connecticut is circled in red. Massachusetts is similarly marked in blue. Both states had non-contiguous territorial claims thanks to intervening states. Image source.

Too small to be states?

Puerto Rico is comparable to modern-day Connecticut in size and population — not including Connecticut’s former Western Reserve, which is now part of Ohio. (Image from 1,2,3,4.)
In order to help justify the admission of Illinois, the Illinois border was extended significantly northwards to include the area that is now Chicago. (Image source.)

A State of the Territories

Puerto Rico is comparable in size and population to Connecticut. The smaller island territories, combined, are roughly the size and population of an average county within in Connecticut. (Sourced from previous and source.)
Left to right: Flags of Guam, Northern Mariana Islands, American Samoa, and U.S. Virgin Islands. (Images from 1,2,3,4.)

A Territorial Representation Amendment

(Image source.)

Annexation into an existing state

For a territory the size of Puerto Rico, large enough to be a state in its own right, this seems particularly unlikely — but this is another possibility that would satisfy democratic principles. (Image from 1,2,3 .)

Independence

Summary

Islands approximately but not perfectly to scale. Some smaller islands not pictured. (Image built from 1,2,3,4.)

Appendix

Puerto Rico

Puerto Rico has been through five status referendum. For 2012, territory votes are from the first question. The PPD had a highly successful boycott in 2017.

U.S. Virgin Islands

The Marianas

American Samoa

Dr. Tomas McIntee is a mathematician and occasional social scientist with stray degrees in physics and philosophy.

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