Bring meat to room temp and season with salt and pepper. Set a rack in the lower third of the oven and preheat to 325°F.
Heat a large Dutch oven over medium-high to high heat. Add olive oil, to coat bottom lightly. Brown meat all over in 2 batches and remove.
Add a little more olive oil to the pan and reduce heat to medium-high. Add celery, onions, peppers, mushrooms, garlic, fennel seeds, chili flakes, sugar or honey, herb bundle and salt, and cook to soften 7-8 minutes. Add wine and reduce by half. Add stock and tomatoes, and bring to boil. Add reserved meat back to the pan and cover. Transfer to oven and cook 2-2 1/2 hours until meat is tender.
Remove herb bundle and serve with bread, Garlicky Mashed Potatoes or polenta alongside.