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The question before the court in the OTL insular cases (1901) was basically "Does the Constitution follow the flag?" SCOTUS ruled that it did not have to. America could annex and rule imperial possessions without having to treat their people as US citizens or without following the rules used on the mainland for establishing territorial self-government and eventual admission into the Union as states equal to all the other states.

The territorial gains of the Spanish-American war, above all, the Philippines, compelled the court to examine these questions.

If the US had somehow acquired imperial possessions it did not intend to let into the Union, say, the Philippines in an earlier Spanish-American war, the Ryukyu islands or possibly had it acquired portions of Mexico, Central America or the Caribbean deemed unassimilable, would the courts have ruled as they did in 1901, or would they insist that any territory taken and retained by the US must be granted the territorial self-government and statehood process?

Would the court's of Roger B. Taney, Salmon P.Chase or Morrisson Waite have ruled any differently than the court of Melville Fuller in 1901 ?
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