Coat a Dutch oven with olive oil and bring to medium-high heat.
Sprinkle the chuck roast generously with salt, add it to the Dutch oven and brown it on all sides. Remove from the pan and reserve.
Drain the excess oil, lower the heat to medium, add a few drops of new oil and add the celery, onions and crushed red pepper to the pan. Season the vegetables with salt and cook until they are soft and very aromatic, 8 to 10 minutes. Add the garlic and cook for 1 to 2 minutes. Add the tomato paste and cook for 1 to 2 minutes. Toss in the vinegar, stir to combine and cook for 2 to 3 minutes. Stir in 3 cups of chicken stock. Taste and adjust the seasoning if needed. Toss in the bay leaves, orange zest, star anise and thyme bundle. Return the meat to the pan, cover and put the Dutch oven in the oven for 1 hour.
Remove the pan from the oven, turn the meat over and check the liquid level. If the liquid level has gone down, add about a half a cup of stock. Return the pan to the oven and cook for another hour.
Remove the pan from the oven. Remove the meat from the pan and add the squash, Jerusalem artichokes and figs. Add the final 1/2 cup of stock and stir to combine. Taste the liquid and adjust seasoning if needed. Return the meat to the pan, cover and cook for another 30 minutes.
Remove the lid to the pan and roast until the squash and Jerusalem artichokes are tender and the liquid is reduced, another 15 to 20 minutes.
Remove the pan from the oven. Remove the meat from the pan and skim off any excess fat from the surface of the cooking liquid, if need be.
Slice the meat in 1/2-inch slices and serve with the veggies and pan juices.