Preheat your oven to 325°F (160°C). Pat the chuck roast completely dry with paper towels. Season generously all over with kosher salt and black pepper.

Heat the olive oil in a large, oven-safe Dutch oven (6-8 quart) over medium-high heat until shimmering. Carefully add the seasoned chuck roast to the hot oil. Sear on all sides, turning with tongs, until deeply browned and caramelized, about 5-7 minutes per side. This step is crucial for flavor development. Remove the seared beef from the Dutch oven and set it aside on a plate.

Reduce the heat to medium. Add the chopped onion, carrots, and celery to the Dutch oven. Sauté for 8-10 minutes, stirring occasionally, until the vegetables have softened and started to brown slightly. Add the minced garlic, dried oregano, and red pepper flakes (if using). Cook for another minute until fragrant, being careful not to burn the garlic.

Stir the tomato paste into the vegetables and cook for 2 minutes, allowing it to deepen in color. Pour in the red wine, scraping the bottom of the Dutch oven with a wooden spoon to deglaze and release all the flavorful browned bits. Bring the wine to a simmer and cook for about 5 minutes, allowing the alcohol to cook off slightly and the liquid to reduce.

Stir in the crushed tomatoes, beef broth, bay leaves, fresh rosemary sprigs, and fresh thyme sprigs. Bring the liquid to a gentle simmer.

Carefully return the seared chuck roast to the Dutch oven, nestling it into the liquid. Ensure the meat is mostly submerged; if not, add a little more beef broth or water. Cover the Dutch oven tightly with its lid.

Transfer the covered Dutch oven to the preheated oven. Braise for 3 to 4 hours, or until the beef is incredibly fork-tender and easily pulls apart. You can flip the roast once or twice during cooking for even braising.

Once cooked, carefully remove the Dutch oven from the oven. Transfer the tender beef to a cutting board, tent it loosely with foil, and let it rest for 15-20 minutes. This allows the juices to redistribute.

While the beef rests, discard the bay leaves, rosemary, and thyme sprigs from the sauce. Taste the sauce and adjust seasonings (salt and pepper) if needed. If desired, you can skim any excess fat from the surface of the sauce. For a smoother sauce, you can use an immersion blender to purée some of the vegetables directly in the pot, or press the sauce through a fine-mesh sieve.

Shred or slice the pot roast against the grain. Serve hot, generously spooning the rich Stracotto sauce over the meat. Enjoy!