Whip the heavy cream with powdered sugar and vanilla until soft peaks form. Set aside.
In a blender, combine the milk, chocolate ice cream, and chocolate syrup. Blend until smooth and creamy.
Pour into a tall glass. Top generously with whipped cream, chocolate chunks, and a drizzle of syrup.
Serve immediately, thick and indulgent, just the way Castro enjoyed them.
Dish Summary: A decadent chocolate milkshake once beloved by Fidel Castro. Indulgent, rich, and tied to one of the most bizarre stories in Cold War history.