Preheat your oven to 300 degrees F (150 degrees C). Thoroughly dry the beef chuck roast with paper towels on all sides, then season evenly with kosher salt and black pepper.

Heat the olive oil in a large Dutch oven or oven-safe heavy pot over medium-high heat. Add the chuck roast and sear undisturbed for 4 to 5 minutes per side until a rich, dark brown crust develops. Transfer the meat to a plate and set aside.

Reduce the heat to medium. Add the onion wedges and smashed garlic cloves to the remaining fat in the pot, cooking for 3 to 4 minutes until golden and fragrant. Stir in the tomato paste and cook for 1 minute.

Pour the red wine into the pot to deglaze, scraping up all browned bits from the bottom with a wooden spoon. Allow the wine to simmer vigorously for 3 minutes until reduced by half.

Pour in the beef broth and Worcestershire sauce. Return the seared chuck roast and any resting juices back to the pot. Nestle the fresh rosemary sprigs, thyme sprigs, and bay leaves into the braising liquid around the meat.

Bring the liquid to a light simmer on the stovetop, cover tightly with the lid, and transfer the pot to the preheated oven. Braise for 2 hours.

Carefully remove the pot from the oven. Arrange the carrot chunks and potatoes around the roast, pressing them down so they are partially submerged in the hot braising liquid. Cover and return to the oven for another 45 minutes, until the vegetables are fork-tender and the beef shreds easily.

Discard the herb stems and bay leaves. Transfer the beef and vegetables to a warm serving platter and tent loosely with foil. Skim off any excess surface fat from the pot juices and simmer on the stovetop until reduced to your desired gravy consistency, then spoon generously over the sliced or shredded meat.