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Preheat your oven to 325°F. Pat the 6 1/4 pounds of beef chuck roast pieces thoroughly dry with paper towels. Season all sides generously with 3 3/4 teaspoons kosher salt and 1 1/4 teaspoons freshly ground black pepper.
Heat the 5 tablespoons of olive oil in a large Dutch oven (at least 7-quart capacity) or oven-safe pot over medium-high heat. Once the oil is shimmering, carefully add the beef pieces and sear until deeply browned on all sides, about 5-8 minutes per side. Work in 2-3 batches if necessary to avoid overcrowding the pot. Remove the seared beef and set aside on a plate.
Reduce the heat to medium. Add the 2 large chopped yellow onions to the same pot and cook, stirring occasionally, until softened and translucent, about 7-9 minutes. Add the 10 minced garlic cloves and cook for another 1 minute until fragrant.
Pour in about 1/2 cup of the unsweetened pear nectar to deglaze the pot, scraping up any browned bits from the bottom with a wooden spoon. This adds rich flavor to the sauce.
Add the remaining 7 1/2 cups unsweetened pear nectar, 2 cups beef broth, 5 tablespoons white wine vinegar, 2 1/2 tablespoons Dijon mustard, 5 bay leaves, and 10 fresh thyme sprigs to the pot. If using, stir in the 2 1/2 tablespoons brown sugar until dissolved. Bring the mixture to a gentle simmer.
Carefully return the seared beef pieces to the Dutch oven, ensuring they are mostly submerged in the liquid. If not, add a small amount of additional pear nectar or water to cover about two-thirds of the beef.
Cover the Dutch oven tightly with its lid and transfer it to the preheated oven. Braise for 3 1/2 hours. After 3 1/2 hours, add the sliced fresh pears to the pot. Continue to braise for another 1 to 1 1/2 hours, or until the beef is incredibly tender and can be easily shredded with a fork, for a total braising time of 4 1/2 to 5 hours.
Carefully remove the Dutch oven from the oven. Transfer the beef and braised pears to a large bowl or cutting board. Remove and discard the bay leaves and thyme sprigs from the braising liquid. Using two forks, shred the beef into bite-sized pieces, discarding any large pieces of fat.
Place the Dutch oven with the braising liquid back on the stovetop over medium-high heat. Bring the liquid to a boil and reduce it by about one-third, stirring occasionally, until it thickens slightly into a rich sauce, about 15-20 minutes.
Return the shredded beef and braised pears to the pot with the reduced sauce. Toss to coat the beef evenly. Serve hot.

Preheat your oven to 325°F. Pat the 6 1/4 pounds of beef chuck roast pieces thoroughly dry with paper towels. Season all sides generously with 3 3/4 teaspoons kosher salt and 1 1/4 teaspoons freshly ground black pepper.
Heat the 5 tablespoons of olive oil in a large Dutch oven (at least 7-quart capacity) or oven-safe pot over medium-high heat. Once the oil is shimmering, carefully add the beef pieces and sear until deeply browned on all sides, about 5-8 minutes per side. Work in 2-3 batches if necessary to avoid overcrowding the pot. Remove the seared beef and set aside on a plate.
Reduce the heat to medium. Add the 2 large chopped yellow onions to the same pot and cook, stirring occasionally, until softened and translucent, about 7-9 minutes. Add the 10 minced garlic cloves and cook for another 1 minute until fragrant.
Pour in about 1/2 cup of the unsweetened pear nectar to deglaze the pot, scraping up any browned bits from the bottom with a wooden spoon. This adds rich flavor to the sauce.
Add the remaining 7 1/2 cups unsweetened pear nectar, 2 cups beef broth, 5 tablespoons white wine vinegar, 2 1/2 tablespoons Dijon mustard, 5 bay leaves, and 10 fresh thyme sprigs to the pot. If using, stir in the 2 1/2 tablespoons brown sugar until dissolved. Bring the mixture to a gentle simmer.
Carefully return the seared beef pieces to the Dutch oven, ensuring they are mostly submerged in the liquid. If not, add a small amount of additional pear nectar or water to cover about two-thirds of the beef.
Cover the Dutch oven tightly with its lid and transfer it to the preheated oven. Braise for 3 1/2 hours. After 3 1/2 hours, add the sliced fresh pears to the pot. Continue to braise for another 1 to 1 1/2 hours, or until the beef is incredibly tender and can be easily shredded with a fork, for a total braising time of 4 1/2 to 5 hours.
Carefully remove the Dutch oven from the oven. Transfer the beef and braised pears to a large bowl or cutting board. Remove and discard the bay leaves and thyme sprigs from the braising liquid. Using two forks, shred the beef into bite-sized pieces, discarding any large pieces of fat.
Place the Dutch oven with the braising liquid back on the stovetop over medium-high heat. Bring the liquid to a boil and reduce it by about one-third, stirring occasionally, until it thickens slightly into a rich sauce, about 15-20 minutes.
Return the shredded beef and braised pears to the pot with the reduced sauce. Toss to coat the beef evenly. Serve hot.