Braised Brisket with Bourbon-Peach Glaze
['1 tablespoon plus 1 teaspoon kosher salt', '1 teaspoon freshly ground black pepper', '1/4 teaspoon smoked paprika', '1/8 teaspoon ground cinnamon', '1 4-pound trimmed flat-cut brisket with about 1/3" top layer of fat', '2 tablespoons grapeseed oil, divided', '3/4 cup chopped onion', '3 garlic cloves, smashed', '4 cups beef broth', '1 12-ounce bottle stout', '3/4 cup bourbon', '1/4 cup (packed) light brown sugar', '1/4 cup soy sauce', '6 large sprigs thyme', '3 celery stalks, chopped', '2 plum tomatoes, cored, chopped', '1 large carrot, chopped', '1 tablespoon balsamic vinegar', '1/2 cup peach jam or preserves', '2 teaspoons bourbon', 'Kosher salt and freshly ground black pepper', 'Ingredient info: Smoked paprika can be found at most supermarkets', 'at specialty foods stores', 'and at latienda.com.']
Mix all ingredients in a small bowl.
Rub brisket all over with spice rub. Cover and chill for at least 2 hours or overnight. Let stand at room temperature for 1 hour before continuing.
Preheat oven to 325°F. Heat 1 tablespoon oil in a large wide pot over high heat. Add brisket, fat side down. Cook undisturbed until well browned, 5-6 minutes. Turn brisket over and cook until browned, about 3 minutes. Using tongs, transfer to a plate. Reduce heat to medium and add remaining 1 tablespoon oil. Add onion and garlic. Cook, stirring occasionally, until onion is slightly golden, about 5 minutes. Add broth and all remaining ingredients. Bring liquid to a simmer. Return brisket to pot. Cover and transfer to oven.
Braise until brisket is very tender to the touch but still holds its shape, about 4 1/2 hours. Using a large spatula, transfer brisket, fat side up, to a large plate. Strain braising liquid into a large bowl. Return liquid to pot, bring to a simmer, and cook until reduced to 2 cups, about 15 minutes. Score fat side of brisket by cutting a crosshatch pattern of 1/4"-deep slits spaced 1/2" apart. Return brisket, fat side up, to pot with reduced braising liquid. DO AHEAD: Brisket can be made 2 days ahead. Return brisket to pot, cover, and chill. Bring to a simmer and rewarm brisket before proceeding.
Transfer 1/4 cup braising liquid to a blender. Add jam and bourbon and purée until smooth. Season with salt and pepper.
Preheat broiler. Spread 3-4 tablespoons glaze on top of brisket with the back of a spoon. Broil brisket in pot until browned and glazed, watching carefully to prevent burning, 4-5 minutes.
Transfer brisket to a cutting board. Slice against the grain and transfer to a large platter. Ladle braising liquid over. Drizzle remaining glaze on top.
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