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Preheat oven to 300°F. Pat brisket dry with paper towels and season with salt and pepper. Heat olive oil in an extra-large skillet (or, alternatively, you can sear your brisket in a heavy bottom roasting pan) over medium-high heat. Once the oil is hot, carefully add the brisket. Sear the brisket until richly seared and dark brown, about 2-3 minutes per side. Remove from the pan and set aside on a large plate or platter.
Add the onions, shallot, and garlic to the pan and sauté for 1-2 minutes. Deglaze the pan with red wine, using your spoon to scrape up any browned bits, bring to a simmer. Once simmering add the vinegar, broth, tomato paste, rosemary, and bay leaves, stir to combine.
Return the brisket to the pan (and any pan juices), nestling it snuggly among the onions. Cover the pan and place it in the oven. Roast for 4-6 hours or until the brisket is fork-tender (this process may take longer depending upon your oven and brisket cut). Remove brisket from the oven and set aside to rest for 30 minutes before slicing and serving. Serve with onions on top and garnish with fresh rosemary.
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