Heat the olive oil in a Dutch oven over medium-high heat. Season the boneless chuck with the salt and pepper and sear on all sides until golden brown, 3 to 4 minutes per side. Remove the beef and set aside.
Place the onion and garlic in the Dutch oven and cook, stirring, until brown and fragrant, about 2 minutes. Add the stock, scraping the bottom of the pot with a wooden spoon to loosen any brown bits, then add the tomatoes and bay leaf.
Return the beef to the pot, cover tightly, and transfer to oven until the beef is fork-tender, 2 1/2 to 3 hours.
Remove the beef to a cutting board and cover it loosely with foil. Transfer the pot to a burner over moderately high heat and bring the liquid to a boil. Remove from heat.
Slice the beef and spoon extra cooking liquid on top.
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