Heat olive oil in a large skillet over medium-high heat. Add onions, garlic, carrots and celery; cook until onions become translucent (about 6-7 mins.) . Add beef and season with salt and pepper. Sauté until browned. Drain fat from pan and add wine, scrapping the brown bits from the bottom of the pan. Continue to cook until wine reduces (about 3-4 mins). Depending on the size of your skillet it may be necessary to cook meat in batches.
Add beef mixture, tomatoes and beef stock to crockpot. Set crockpot to “LOW” and cook for 6 hours.
After 6 hours, taste and add salt/pepper if necessary. Stir in half & half and serve over your favorite pasta, spaghetti squash or zucchini noodles, or over polenta. Garnish with fresh grated Parmesan cheese and chopped Italian parsley.