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Preheat your oven to 300°F.
Season the chuck roast generously with salt and pepper.
In a Dutch oven, heat olive oil over medium-high heat; sear the roast until golden brown on both sides.
Remove the roast and use the same pot to caramelize sliced onions in butter for about 25-30 minutes.
Add garlic, then deglaze with grape juice; let it reduce by half. Stir in flour.
Mix in beef broth, Worcestershire sauce, herbs, and return the roast to the pot.
Cover and braise in the oven for about 3.5 hours until tender.
Shred beef, top with cheese, and return to oven until melted.
Serve warm over mashed potatoes or with toasted baguette slices.