That’s the title of my weekend article over at RealClearHistory. An excerpt:

9. Puerto Rico. Officially an unincorporated territory of the United States, Puerto Rico was acquired by Washington, along with Cuba and the Philippines, in the course of the Spanish-American War of 1898. Not quite an annexed state and not quite a colony, the island has been in legal limbo since the war with Spain ended. In 2017, a referendum was held on the issue of statehood (the fifth of its kind since 1952), and an overwhelming majority of those who voted preferred statehood to independence or the status quo.

Unfortunately, “those who voted” only accounted for about 23% of the island’s population, and referendum was popularly-held, meaning that the legislature didn’t vote on the matter (which is what the federal congress would require in order to consider a Puerto Rican application). Despite the odds being stacked against a Spanish-speaking state, there has never been a better time than now to join the union, especially if representatives could work in tandem with representatives of Jefferson. The history of American statehood is one of balance in the Senate. If Maine could join as a free state, then Missouri could join as a slave state. If Hawaii could join as a blue state, then Alaska could join as a red state. If Puerto Rico joined the union it would be as a blue state, and Jefferson could be the red yang to San Juan’s yin.

Read the rest.