Preheat a large Dutch oven over medium heat. Season the beef chuck roast generously with salt and pepper, then add 1 tablespoon of olive oil to the hot pot. Sear the roast for 10–12 minutes, turning occasionally, until it’s browned on all sides.

Remove the roast from the pot and set it aside. Add another tablespoon of olive oil and sauté the sliced yellow onions for about 5 minutes, stirring frequently, until they become translucent.

Reduce heat slightly and continue cooking the onions for an additional 20 minutes, stirring regularly, until they turn light golden. Add minced garlic and 1 tablespoon of maple syrup or brown sugar for the last 7–8 minutes.

Sprinkle 1 tablespoon of flour over the caramelized onions, stir well, then pour in ½ cup of red wine (if using) and scrape up any bits. Mix in approximately 2.5 cups of beef broth.

Return the seared roast to the pot. Tuck in sprigs of fresh rosemary and a bay leaf. Bring to a simmer over medium heat before covering.

Transfer the covered Dutch oven to a preheated oven at 300°F. Let it braise for about 3 to 3.5 hours until the meat is fork-tender.

Remove the pot from the oven and let the roast rest for 15–20 minutes before shredding with two forks.