makes eight servings
1 3½ pound well-marbled beef chuck roast
1 tablespoon kosher salt
3 tablespoons olive oil
6 ounces thick sliced, center-cut applewood smoked bacon, cut into ½-inch pieces
1 medium butternut squash, peeled, seeded, and cut into 1-inch pieces (about 4 cups)
2 tablespoons unsalted butter
2 cups diced yellow onions
1 leek, white part only, split lengthwise (then blotted dry (reserve one long inner piece) and cut crosswide into slices
3 large cloves garlic, peeled, and roughly chopped (about 1 heaping tablespoon)
2 3/4 cups dry red wine (such as Pinot Noir)
1 cups chicken stock
1 stick cinnamon, broken
2 whole cloves
7 whole black peppercorns
3 fresh bay leaves (or 1 dried bay leaf)
1 tablespoon tomato paste
1/4 teaspoon dried thyme
5 stems fresh parsley, leaves picked and chopped, stems reserved
1 cup pitted prunes
Trim and cut roast into 2-inch pieces. Sprinkle evenly with the 1 tablespoon kosher salt. Cover; chill overnight.
Preheat oven to 450ºF. Line a 15x10x1-inch baking pan with a silicone baking mat; set aside. Cook bacon in 1 tablespoon hot oil over medium-low heat until browned. Remove; drain on paper towel, reserving 3 tablespoons drippings. Place squash on prepared pan. Add 1 tablespoon butter and 1 tablespoon bacon drippings. Sprinkle salt; toss to coat. Roast 20 to 30 minutes or until tender and browned, stirring once. Cover with waxed paper; set aside. Reduce oven to 275ºF.
Add remaining 2 tablespoons. olive oil to remaining 2 tablespoons bacon drippings in skillet; heat over medium-high heat. Blot beef well with paper towels; add to skillet in batches, being careful not to crowd the skillet. Brown deeply on all sides. Remove; set aside.
Drain all but 1 tsp. fat from skillet. Add remaining 1 tablespoon butter and onions to pan. Sprinkle with salt. Stir over medium heat, scraping up browned bits from bottom of pan. Cook 3 to 4 minutes, stirring often, until onions just begin to soften. Stir in leek slices and garlic. Sprinkle with salt. Cook 4 minutes more. Transfer to a 3-quart baking dish; set aside. Pour wine into skillet. Bring to boiling; reduce heat. Boil gently, uncovered, until reduced by half.
Place beef and bacon over onions. Pour reduced wine over. Add stock to almost cover. Using kitchen string, tie cinnamon, cloves, and peppercorns in a piece of cheesecloth; tuck into beef mixture. Add bay leaves. Dollop tomato paste around beef mixture. Sprinkle with thyme. Tie together parsley stems and inner leek piece; add to beef mixture. Place parchment paper over dish. Top with a triple layer of heavy foil. Seal tightly. Place on rimmed baking sheet. Bake 2 hours. Uncover; add prunes. Cover; bake 45 minutes to an hour more or until meat is easily pierced with a knife. Uncover; skim fat. Remove cheesecloth bag and parsley stems; discard. Increase oven to 350ºF. Add butternut squash. Bake uncovered, 20 minutes, basting once or twice. To serve, sprinkle with parsley leaves.