Tie each shank piece tightly around the circumference with twine. Then season with the salt and pepper and lightly coat with flour.
In a large pot heat up the oil. Once hot, layer the meat in a single layer, no overlapping, and brown on all sides.
Remove the meat from the pot and set aside. Add to the pot onions, carrots, celery, and garlic. Lightly brown them.
Return the meat to the pan and add red wine and let simmer for approximately 10 minutes.
Add the tomatoes, beef stock. Cover with foil and place in the oven for 325°F for 2 hours or until tender.
Season to taste with salt and pepper.