Heat 1 tablespoon extra virgin olive oil in a wide pot over medium heat. Add the beef and season with salt and pepper. Cook for 10 minutes, breaking up with a spoon, until the beef is browned in spots and almost cooked through.

Add the diced onion, celery, and carrots to the beef. Sauté for 10 minutes until the vegetables soften. Add a pinch of salt and pepper.

Add the minced garlic and Castelvetrano olives. Toss to coat and cook for 1 to 2 minutes. Add the diced tomatoes and crushed red pepper along with 1 cup water. Bring to a boil.

Reduce the heat to low. Cover and simmer for 30 to 45 minutes. Stir the sauce occasionally and add more liquid as needed if it reduces too quickly. Taste and adjust the seasonings to your preference.

Bring a large pot of generously salted water to a boil. Cook the pasta according to package directions. Reserve ½ cup of the pasta water and drain the pasta. Set aside.

Remove the cover from the sauce and return it to a low boil. Add the pasta cooking water, grated Parmigiano Reggiano, and the minced oregano. Stir until the cheese melts. Reduce the heat to medium-low, and add the cooked pasta. Toss to coat for 1 to 2 minutes. Taste and season. Turn off the heat.

Transfer the pasta to a large serving bowl. Finish with more grated Parmigiano Reggiano and fresh oregano leaves if desired. Enjoy!