Let's look back real quick at Rule #6 in the Platt Amendment. It says that "the Isle of Pines shall be omitted from the proposed constitutional boundaries of Cuba" (VI). The Isle of Pines was a small piece of land in Cuba, and the U.S. was looking to stake a claim on the island in the future.

Why? All sorts of reasons—economic gain through resource-collecting, creating military bases, keeping an eye on Cuba, establishing a port, etc.

But then someone got sued. A few years after the Platt Amendment was made law, a dude named Pearcy brought a bunch of Cuban cigars from the Isle of Pines into New York City. The port authorities tried to tax the cigars because they came "from another country" (that'd be Cuba). Pearcy said no way, because the Isle of Pines is part of the U.S. according to the Platt Amendment.

But here's where it gets muddy. Look back at the wording in the Platt Amendment—does it actually say that the Isle of Pines, with apparently some decent cigar production, belongs to America? It leaves things pretty vague, doesn't it?

You might be surprised by what the court said—the Isle of Pines doesn't strictly belong to the U.S., and since it used to be part of Spain's Cuba, it will be considered part of Cuba's Cuba. So essentially, this court ruling went against the Platt Amendment.

This was the first time the Platt Amendment was challenged, but it wouldn't be the last.