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Place tomatoes in a bowl, add 1 tablespoon of the oil, season with salt and pepper and toss. Add leaves from 4 branches of the thyme, toss again, then spread the tomatoes in a single layer on a foil-lined baking sheet, skin side down. Set aside.
Heat remaining oil in an ovenproof casserole on medium high. Dry meat and sear in several batches to avoid crowding until lightly browned on all sides. Remove to a bowl. Lower heat to medium low. Heat oven to 300 degrees.
Add fennel, leeks, shallot and garlic to casserole, stir, season with salt and pepper and cook until lightly browned. Stir in the flour, cook for a moment or two, than add olives, chile flakes and wine. Stir, scraping pan, and bring to a simmer. Add stock. Return meat and its juices to the casserole. Top with branches of rosemary and remaining thyme. Cover and place in the oven. Place the pan of tomatoes in the oven. Cook both for 2 hours.
Remove the pans from the oven. Check seasonings of meat. Transfer meat and sauce to a serving dish, arrange tomatoes on top and serve together.