Begin by patting the beef chuck roast dry with paper towels. Season all sides with kosher salt, black pepper, and garlic powder. Dust with all-purpose flour if desired.

In a large Dutch oven, heat olive oil over medium-high heat. Sear the seasoned roast for about 3 to 4 minutes per side until golden brown.

Remove the roast and sauté diced onion, chopped carrots, and chopped celery over medium heat for 5-6 minutes. Add minced garlic, tomato paste, oregano, thyme, and bay leaf.

Pour in unsweetened grape juice, scraping the pot to deglaze. Then add crushed tomatoes, beef broth, and balsamic vinegar, stirring to combine.

Return the roast to the pot, partially submerging it. Bring to a simmer, cover, and reduce heat to low. Cook for 3 to 3½ hours until fork-tender.

After cooking, remove the roast and let it rest for 10 minutes. Slice or shred the meat and return to the sauce. Serve with sides.