What could be more comforting than pot roast paired with a glass of Tuscan Sangiovese.
Preheat the oven to 375 degrees F. Trim the meat of any fat. Season with salt and pepper.In a large dutch oven, heat the olive oil and sear the meat on all sides. Remove the meat to a platter and add the onions, leeks, celery, carrots, and garlic. Cook the vegetables over medium heat until onions are translucent and the vegetables have taken on a golden color.
Return the beef to the pot and add red chile flakes, red wine, beef broth, tomatoes, and herbs. Bring to a boil. Cover and transfer to the oven for 2-1/2 hours or until meat is tender and falling apart.
Remove the meat from the pot and strain the liquid from the vegetables. Set the vegetables aside and return the strained liquid to the pot. Skim off any fat on top of the liquid.
Over high heat reduce the liquid by about one-third. Taste for seasoning, add salt and pepper if needed. Return the meat and vegetables to the pot and warm throughly.
Slice the meat and serve in shallow bowls with vegetables and the reduced sauce. Sautéed shiitake mushrooms and mashed potatoes as sides.