Start by seasoning the beef chuck roast generously with salt and pepper on all sides.
In a large Dutch oven or heavy pot, heat the olive oil over medium-high heat. Once hot, sear the roast on all sides until browned (about 3-4 minutes per side). Remove the roast and set aside.
In the same pot, add the sliced onions and cook until softened, about 5 minutes. Add the minced garlic and sauté for an additional 1-2 minutes until fragrant.
Stir in the carrots and celery, cooking for about 3-4 minutes until they begin to soften.
Add in the diced tomatoes with their juice, beef broth, oregano, basil, and red pepper flakes. Stir well to combine all the flavors.
Return the seared roast to the pot, nestling it among the vegetables and liquid. Bring to a simmer, then cover and reduce the heat to low.
Let it cook slowly for about 3-4 hours, or until the roast is tender and easily pulls apart with a fork. Alternatively, you can cook it in a slow cooker on low for 6-7 hours.
Once done, remove the roast and let it rest for a few minutes before slicing.
Serve the sliced roast with a generous ladle of the sauce and vegetables over pasta or mashed potatoes.
Notes
Serve with crusty bread and garnish with fresh basil for added flavor.