Roasting and then broiling the canned tomatoes first browns them and deepens their flavor, adding even more robust tones to this hearty dish.
2 (28-ounce) cans of whole peeled tomatoes
4 tablespoons extra-virgin olive oil
1 (5- to 6- pound) beef brisket, fat cap intact
Kosher salt and freshly ground black pepper
12 ounces cremini mushrooms, thinly sliced (2 cups)
2 large yellow onions, diced
6 garlic cloves, smashed and peeled
1 cup red wine
2 large carrots, scrubbed and cut into 1-inch pieces
12 sprigs thyme
4 fresh bay leaves
To make the Roasted Tomato Brisket:
Preheat the oven to 450°F.
Pour the canned tomatoes and all their liquid into a 9 by 13-inch metal baking pan and spread them into an even layer. Drizzle 1 tablespoon of olive oil on top. Roast for 30 minutes. Move the dish to the top rack of the oven, then turn on the broiler and broil for 3 to 4 minutes, until the tops of the tomatoes begin to lightly char. Remove from the oven and let cool slightly, then carefully mash the tomatoes with the back of a fork or a potato masher. Reduce the oven temperature to 325°F.
Season each side of the brisket with 2 heavy pinches each of salt and pepper. In a large Dutch oven, heat the remaining 3 tablespoons olive oil over medium-high heat. Sear the brisket, turning it as needed, until golden brown, 15 to 20 minutes. Transfer the brisket to a platter.
Reduce the heat to medium, then add the mushrooms, onions, and garlic to the pot. Cook, stirring often, until softened and lightly caramelized, 10 to 15 minutes. Add the wine, then stir continuously with a wooden spoon for 1 minute to scrape up any browned bits on the bottom of the pot.
Stir in the roasted tomatoes, carrots, and 2 heavy pinches each of salt and pepper, then return the brisket to the pot. Tie together the thyme sprigs and bay leaves with a small piece of butcher’s twine (tying is optional, but makes it much easier to remove the herbs after cooking) and nestle the herb bundle in the pot. Bring to a simmer, then cover the pot and transfer to the oven. Cook for 3 hours to 3 hours 30 minutes, until very tender when pierced with a fork. Remove from the oven and let cool completely, then refrigerate overnight.
The next day, skim off and discard any fat if desired, and discard the herbs. Transfer the brisket to a cutting board and cut it across the grain (perpendicular to the fibers you’ll see running through the brisket) into ¼-inch-thick slices. Return the meat to the sauce and heat over medium heat until warmed through. Taste and adjust the seasoning with salt and pepper, then serve.
Buying Brisket 101:
Beef briskets come in many shapes and sizes (just like us!), but it all comes down to choosing between the first (or flat) cut and the second (or point) cut. The flat is much leaner, and often smaller, made up of one muscle cleaned of most fat. The point, my preferred cut, contains the deckle, a gorgeous layer of the fat and muscle attached to the rib cage. More fat equals more flavor, so don’t deprive yourself of the deckle! As for the size, I find 5 to 6 pounds is the sweet spot for yielding a ton of brisket while still being manageable for even my tiny NYC kitchen.