Brisket is often part of a traditional Passover meal. This rendition is oven-braised low and slow with red wine and aromatics; the meal is completed by a head of garlic and tender root vegetables.
Whole brisket typically weighs 8 to 12 pounds and is sold cut into 2 pieces -- the first (or flat) cut and the second (or point) cut. Select a first cut that's evenly thick with a cap of fat on one side. For an extra-moist brisket, don't trim the fat.
Preheat oven to 325 degrees. Season both sides of brisket with salt and pepper. Place a roasting pan across 2 burners on medium-high. Heat 3 tablespoons oil in pan. Add brisket; sear until browned, 4 to 5 minutes per side. Transfer to a plate.
Reduce heat to medium. Add onion and minced garlic to pan; cook, stirring often, until onion is soft, about 4 minutes. (Add more oil to pan if needed.) Stir in tomato paste, and cook for 1 minute more. Stir in wine, and cook, scraping any browned bits from bottom of pan.
Add stock and bay leaves, and bring to a boil. Add the brisket to the pan, and cover with foil. Transfer to oven, and roast until meat is very tender, about 2 hours. Flip meat over. Add head of garlic. Cover, and roast for 30 minutes more.
Add remaining vegetables to brisket, cover, and roast until meat and vegetables are tender, about 1 hour. Transfer vegetables and garlic to a platter and meat to a cutting board, reserving pan sauce. Tent meat with foil; let rest.
Let sauce stand in pan for 15 minutes, then skim fat from top. Place pan across 2 burners over medium-high heat; cook until sauce is reduced by slightly more than half, about 20 minutes. (You should have about 2 cups.) Stir in vinegar.
Thinly slice brisket against the grain. Arrange slices on a platter with the vegetables. Season with pepper, and drizzle with some sauce. Serve immediately with remaining sauce.
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