Cook the 1 pound spaghetti in generously salted water according to package instructions, until al dente. Before draining, reserve 1 cup of the pasta water.
Heat the 2 tablespoons olive oil in a large skillet or Dutch oven over medium high heat. Add the 1 pound ground beef and cook for about 3 minutes, breaking it up as you go, until no longer pink.
Add the 1 chopped onion and 4 cloves minced garlic and cook for another 3 minutes, until the onion has softened.
Add the 1 tablespoon dried oregano, ¼ teaspoon red pepper flakes, and 2 tablespoons tomato paste. Stir and cook for a full minute, until the paste darkens slightly and smells rich. Pour in the 1 cup red wine and cook for about 5 minutes, until most of the liquid has cooked off.
Add the 28 ounces crushed tomatoes and 2 tablespoons chopped basil, then season with the ½ teaspoon salt and ½ teaspoon pepper. Bring to a boil, then reduce the heat to medium low, cover, and simmer for 20 minutes.
Reduce the heat so the sauce is at a gentle simmer, then stir in the ¼ cup heavy cream. The sauce will deepen in color and thicken slightly. Taste and adjust the seasoning.
Add the cooked spaghetti to the pot and toss until every strand is coated, loosening with the reserved pasta water if needed. Let it sit for a minute, then top with the ½ cup grated Parmesan and the remaining 2 tablespoons basil.