How to Make It
Light a grill. In a small skillet, heat the 2 tablespoons of olive oil. Add the chorizo and cook over low heat, stirring occasionally, until crisp, about 8 minutes. With a slotted spoon, transfer the chorizo to a plate. Pour the leftover oil into a small bowl, whisk in the vinegar and season with salt.
Drizzle the asparagus with olive oil and sprinkle with salt. Grill over moderately high heat, turning often, until lightly charred and just cooked through, about 5 minutes. Transfer the asparagus to a plate. Grill the pineapple slices on one side, about 30 seconds. Cut the pineapple slices into half-moons and remove the core; transfer to the plate with the asparagus.
On a work surface, place 4 asparagus spears in the center of each prosciutto slice and roll into a bundle. Arrange 2 pieces of pineapple on each plate and top with the asparagus bundles. Spoon some of the dressing over the top, sprinkle with the chorizo and serve.