Preheat a Dutch oven over medium-high heat and add a drizzle of extra virgin olive oil. Season the chuck roast generously with sea salt and freshly ground black pepper, then sear each side for 10-12 minutes until browned.

Remove the roast and set aside. In the same pot, add sliced yellow onions and sauté for 5 minutes until translucent, then continue cooking on medium for an additional 20 minutes until caramelized.

Stir in minced garlic and maple syrup or brown sugar for 7-8 minutes. Add flour, stir to coat, and deglaze with red wine, scraping up any browned bits. Pour in beef stock and check seasoning.

Nestle the roast back into the pot, submerging it in onion mixture. Add rosemary and bay leaf, bring to a simmer, cover, and transfer to a preheated oven at 300°F for 3 hours.

Once done, let the roast rest for 10 minutes before slicing. Serve alongside creamy mashed potatoes or polenta, drenching in onion gravy.