Chapter 5 reflects on the role of US neocolonialism from the eve of the Great War to the mid-1920s. In 1916, anarchists launched the first general strike against the US-controlled Panama Canal. Several months later, both Panama and Cuba declared war on Germany within hours of President Wilson’s war declaration. Cuba developed a military draft law modeled on the US law. Puerto Rico’s residents acquired US citizenship in 1917, and thus the island’s male population became eligible for the draft. Anarchists throughout the network emerged to challenge this new wave of regional militarism. Around the same time in Puerto Rico, a pro-independence movement began forming. Anarchists debated the meaning of the island’s independence from the USA, asking just how “free” and independent could a nation be in the “American Mediterranean”? Finally, anarchists began a campaign to counter the growing US friendship with dictators who ruled so-called “banana republics” for the benefit of US corporations. As such, anarchists continued their long critique of US expansionism in the Caribbean, reflecting their long role as anti-imperialist actors in Latin America.