Separate the raw ground beef into 3 equal portions and pat dry thoroughly with paper towels. Heat 2 to 3 tablespoons of the olive oil in a large frying pan over medium-high heat; add 1 portion of the meat and sauté, breaking up the meat with a wooden spoon, until thoroughly browned, 5 to 7 minutes; and then, with a slotted spoon, transfer the browned meat to a large mixing bowl. A batch at a time, using the fat already in the pan, brown the remaining beef in the same way.

Add the remaining olive oil to a large stockpot over medium heat and sauté the onions and carrots until soft, about 10 minutes, covering the pot for the last 2 minutes. Uncover the pot cover and add the garlic, sautéing for 1 to 2 minutes. Stir in the cooked beef and oregano. Stir in the milk and simmer until no excess liquid remains, about 10 minutes. Add 1 cup of the port wine simmer until no excess liquid remains, about 7 minutes.

Thoroughly stir in the marinara, sugar, and bay leaves. Reduce the heat to low, add the remaining port, and simmer for about 1 hour, stirring occasionally. Remove from the heat and leave briefly to cool; then, skim off any fat from the surface. Discard the bay leaves and use serve immediately over cooked pasta, garnishing with chopped fresh basil and, if you like, small basil sprigs. Refrigerate overnight and reheat the next day for even better flavor.