One of the best ways to squeeze the last vestiges of flavor out of the local tomato crop in the early fall is to roast them. It is a simple process that concentrates their natural sweetness and adds a delicate smokiness, which is ideal for chili. Add some melt-in-your-mouth brisket and a dash of heat and you have a Northeastern dish that would make a Southern pit master proud. This is version is best enjoyed with a beer in one hand and a hunk of cornbread in the other.
4 pounds fresh tomatoes (preferably plum tomatoes but any variety would do), or 2 (15-ounce) cans fire-roasted tomatoes, drained (in the off-season)
4 tablespoons olive oil, divided
1½ tablespoons chipotle chili powder
2 teaspoons cinnamon
1 teaspoon cumin
½ teaspoon cayenne pepper powder
½ teaspoon ground coriander
1½ cups water, divided
2 tablespoons canola oil
1 (3½-pound) flat-cut beef brisket, trimmed and cut into 1-inch cubes medium yellow onions, diced
4 cloves garlic, minced
1 yellow bell pepper, seeded and diced 1 (12-ounce) beer
1 cup beef stock
Sour cream and shredded cheddar cheese for serving
To fire-roast the tomatoes: Remove stems and cut in half. Place tomatoes cut side down on a baking sheet lined with parchment paper (you may need 2) and brush with 1 tablespoon olive oil. Place tomatoes on the top rack of the oven and turn broiler to high. Let cook for 10 minutes, until skins begin to blister (but watch carefully so they don’t incinerate). Remove from oven and let stand until they are cool enough to handle. Remove the skins (they should slip right off).
Change oven temperature to 350°F. Place the peeled tomatoes back on the baking sheets and drizzle with an additional tablespoon of olive oil, sprinkle with ½ tablespoon kosher salt and 1 teaspoon black pepper. Place on the middle rack of the oven and let cook 45 minutes to an hour, until their juices have mostly evaporated and they appear slightly dehydrated.
Once cool, combine the tomatoes and any remaining juices, all spices, 1 cup water, ½ tablespoon of kosher salt and a teaspoon of black pepper in a blender (this may need to be done in batches). Blend together, adding more water slowly if necessary to loosen mixture. Set aside.
Leave the oven set to 350°F. Heat 2 tablespoons canola oil over medium-high heat in a large stockpot on the stove.
Season the cubed brisket with kosher salt and black pepper, then brown it in 3 batches, setting the meat aside as browned. Once all the meat is browned, add remaining olive oil, onion, garlic and pepper to pot. Cook, stirring occasionally, until vegetables soften. Turn heat to low and add beer to deglaze the pot. Stir and scrape up browned bits, cook 3 minutes, then remove from heat. Add the browned meat, beef stock and the blended tomato mixture to the pot. Meat and vegetables should be fully immersed—add water if needed. Cover the pot and place in the center of the oven and cook for 1–2 hours, or until meat is tender.
Skim any fat off the top of the pot before serving with sour cream and shredded cheese.
BETHANY GRABER is a Boston-based food writer whose work can be seen in The Boston Globe, Edible Boston and on her blog winedinerepeat.com. A lover of coffee and a glutton for pastry, she and her insatiable appetite can be found eating their way through the city or at email@example.com.