In a large skillet over medium heat, heat oil. Add onion, carrot, celery, and garlic and cook until tender, 6 minutes. Add tomato paste and stir until combined, then add ground beef and brown. Transfer mixture with a slotted spoon to slow-cooker.
Add crushed tomatoes, oregano, thyme, bay leaf, salt, red wine, and milk. Stir until combined, then season with pepper. Cover and cook on low, 6 hours. Discard bay leaf.
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