Place bacon in a large skillet and cook over medium-high heat, turning occasionally, until evenly browned, about 10 minutes. Drain the bacon slices on paper towels and crumble.
Place potatoes into a large pot and cover with salted water; bring to a boil. Reduce heat to medium-low and simmer until slightly tender, about 8 minutes. Drain and transfer potatoes to a baking dish. Drizzle olive oil over potatoes and season with black pepper.
Bake in the preheated oven until tender, about 10 minutes.
Mix potatoes, bacon bits, Caesar salad dressing, and green onions together in a bowl. Serve warm.