In a large saucepan, combine the potatoes and enough cold water to cover by 1 inch. Bring to a boil and cook until fork-tender, about 20 minutes. Drain and return to the pot.
Using the back of a large spoon, lightly smash the potatoes. Stir in 1/4 cup olive oil and season with salt and pepper. To serve, drizzle each portion with 1/2 tablespoon olive oil.