Preheat oven to 325°F.
Season the chuck roast generously on all sides with salt and pepper.
Heat the olive oil in a large Dutch oven or heavy-bottomed pot over medium-high heat. Sear the roast on all sides until well-browned, about 8-10 minutes total. Transfer the roast to a plate.
Add the onions and garlic to the pot and cook for 2-3 minutes until fragrant.
Whisk in the red wine (if using), beef broth, tomato paste, and Worcestershire sauce. Bring to a simmer, scraping up any browned bits from the bottom of the pot.
Return the roast to the pot and add the bay leaves. Cover and transfer to the oven. Cook for 1 hour per pound of meat, so a 4 lb roast will take about 4 hours.
After 3 hours, add the potatoes, carrots, and celery to the pot. Cover and continue cooking until the meat is fork-tender, about 1 more hour.
Remove the roast from the pot and let rest for 15 minutes. Shred the meat using two forks.
Increase the oven temperature to 425°F. Toss the shredded meat back into the pot with the vegetables and cooking liquid. Roast uncovered for 25 minutes to crisp up the edges.
Serve hot and enjoy!