Steak Pizzaiola

Serves 6 to 8
The caramelized tomatoey-beefy aroma when it is cooking is indescribably inviting and memorable. All you need are just a few ingredients and some time. The whole thing is cooked in one large ovenproof skillet, which works its magic untended once it is placed in the oven. When it’s done the meat is easy to shred, with a robe of thickened tomato sauce clinging to it. Serve with bread or polenta and sautéed Swiss chard on the side. Or, present it as a “sauce,” with all the meat shredded uniformly and tossed with a pound of big, boy-size pasta such as rigatoni and with a fluffy cloud of grated Parmesan cheese on top. This dish will never disappoint, and it could become your favorite dinner, both to make and to eat.


  • 2 1/2 pounds bone-in chuck steak, or 2 pounds if boneless
  • 1 teaspoon coarse salt
  • Freshly ground black pepper
  • 2 tablespoons extra-virgin olive oil
  • 3 to 4 garlic cloves, minced
  • 1 teaspoon dried oregano
  • 1 teaspoon dried thyme
  • 1/4 teaspoon crushed red pepper flakes
  • 1 tablespoon tomato paste
  • 1 28-ounce can whole tomatoes, with juice


  1. Preheat the oven to 325 degrees Fahrenheit. Season the meat on both sides with salt and pepper. Heat a large ovenproof skillet over high heat and swirl in the olive oil. Brown the meat on both sides. Remove the meat from the skillet and take the pan off the heat.
  2. Stir into the pan the garlic, oregano, thyme, red pepper flakes, tomato paste, and whole tomatoes. Mash up the tomatoes with the back of a spoon, return the meat to the pan, spoon the sauce over it, and cover tightly.
  3. Braise in the oven for at least 2 hours, stirring occasionally. Uncover and cook for an additional 30 minutes, until the sauce has thickened up.
cook's note
Chuck Steak The secret of this dish is to use fatty meat with big bones, such as chuck steak, one of the most affordable and flavorful cuts of meat you can buy, which makes it perfect for guys. It’s browned first, then slowly simmered in liquid until it becomes meltingly tender.

All Canned Tomatoes Are Not Created Equal Among available commercial brands, taste, acidity, and sweetness can vary. Muir Glen organic variety, my favorite, delivers a consistent, balanced flavor. Some of the imported Italian San Marzano tomatoes are excellent, too, but many others aren’t. American brands are also of widely varied quality. Always taste your tomatoes first; if they have a strong acidic tang, then add up to ½ teaspoon of sugar per can to the tomatoes during cooking.
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