Preheat oven to 350ºF. Pat the chuck roast dry and cut into 2” cubes. Season all over with salt and pepper. Dice the onion. Peel and trim the carrots and cut into 3” pieces. Cut the garlic in half cross-wise.

In a large oven-proof pot, head the oil over medium high until very hot. Add the beef in an even layer, cooking in batches if necessary. Cook the beef for about 3-5 minutes per side or until well-browned all over and transfer to a bowl. Set aside.

Turn the heat on the pot to medium and add the diced onion. Cook for 8-10 minutes or until well-browned and softened all over. Add the tomato paste and stir regularly until the paste begins to deepen in color. Pour in the beef stock and red wine and scrape up any browned bits stuck to the bottom of the pot. Add the can of crushed tomatoes and the carrots and bring to a boil. Add the beef along with any juices in the bowl to the pot. Taste and season lightly with salt, pepper, and crushed red pepper.

Place the garlic, cut-side up, on top of the stew and do not submerge the garlic under the liquid. You want the cut side of the garlic to be exposed as it roasts. Drizzle the garlic lightly with oil and sprinkle with sea salt and crushed red pepper. Transfer the pot to the oven and bake for 2½-3 hours or until the beef is very tender and falling apart and the garlic is well-browned. Be sure to stir the stew every hour or so. If the garlic seems very dry, add another small drizzle of oil.

About 30 minutes before the stew is finished cooking, carefully remove the garlic from the stew and transfer to a plate to cool. Once the garlic is cool enough to handle, pop the cloves out of the skin. Roughly chop the cloves and stir back into the stew and allow to bake for an additional 10-15 minutes.

Ladle the beef stew with garlic into bowls and serve with toasted bread, egg noodles, or mashed potatoes. Garnish with fresh chopped parsley or chives or a drizzle of cream, if desired. Enjoy!