Heat the olive oil in a Dutch oven or other heavy pot over medium-high heat. Season the beef pieces on all sides with the salt and pepper. Add the beef to the pan and sear on all sides until browned, 2 minutes per side. Remove beef to a clean plate.
2 tablespoons olive oil, 2-2.5 pound boneless beef chuck roast, 1 teaspoon salt, ½ teaspoon black pepper
Add the onion, carrot and celery to the pot and cook, stirring often, for 4-5 minutes, until softened. Add the garlic and cook, stirring, for 30 seconds.
1 cup diced yellow onion, 1 large carrot, 2 ribs celery, 5 cloves garlic
Add the tomato paste and red wine and cook for 2-3 minutes, stirring and scraping up any browned bits from the bottom of the pan.
6 ounce can tomato paste, 1 cup red wine
Add the crushed tomatoes, dried oregano, dried thyme and bay leaves. Stir. Return the beef to the pot, along with any juices from the plate.
28 ounce can crushed tomatoes, 1 teaspoon dried oregano, ½ teaspoon dried thyme, 2 bay leaves
Cover and cook over low heat (it should be simmering very gently) for 2.5-3 hours, until beef shreds easily with a fork. You can uncover the pot during the last 30 minutes or so of cooking to thicken up the sauce if needed.
Remove and discard bay leaves. Transfer the beef to a bowl or cutting board and shred with two forks, discarding excess fat. Stir the beef back into the sauce in the pot.
Season to taste with more salt and pepper, if needed. If the sauce tastes a bit flat, stir in the 1 teaspoon of balsamic vinegar.
1 teaspoon good-quality balsamic vinegar
Serve beef ragu over pasta (pappardelle or fettuccine are my top choices), spaghetti squash or polenta and enjoy!