Preheat the oven to 325 degrees F. Place an oven rack on the lower third shelf.
Pat the chuck roast dry with paper towels. Season all sides with the salt and pepper, then lightly dust with some of the flour.
Heat the olive oil in a large dutch oven set over medium-high heat. Sear the roast until browned on all sides, about 4-5 minutes per side. Transfer to a plate. Lower the heat to medium.
Add the pearl onions and carrots to the pot. Cook, stirring occasionally, until lightly browned, about 5 minutes.
Stir in the garlic, tomato paste, and remaining flour. Cook for 1 minute, stirring constantly.
Pour in the red wine and scrape up any browned bits from the bottom of the pot. Simmer for 5 minutes to reduce slightly.
Stir in the beef broth, rosemary, thyme, bay leaves, and Worcestershire sauce.
Return the roast to the pot, nestling it into the liquid. The liquid should come about halfway up the sides of the meat.
Cover and transfer to the oven. Cook until the beef is fork-tender and easily shreds, about 3-3 1/2 hours.
Transfer the roast to a serving platter and tent loosely with foil until ready to serve. Discard the herb stems and bay leaves.
Place the dutch oven over medium heat and simmer the sauce for 5-10 minutes to thicken slightly.
Slice or shred the beef and serve with the carrots, pearl onions, and sauce spooned over the top. Garnish with the parsley before serving.