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Step 1
Roast the peppers: Position a rack about 6 inches from the broiling element and preheat the broiler. Arrange the peppers on a large, rimmed baking sheet and broil, turning every 3 to 5 minutes with tongs, or until they are blistered all over and collapsing on themselves, 15 to 20 minutes total. (Keep an eye on the peppers as they can go over the edge in seconds.) Transfer the peppers to a medium bowl, cover with a wide plate and let sit until cool enough to handle, about 30 minutes. Remove and discard the skins and seeds, slice the peppers into 1/2-inch-wide strips and set aside on the cutting board. If not using right away, transfer to a lidded container and refrigerate until needed.
Step 2
Make the chicken: While the peppers are cooling, in a large Dutch oven or other heavy-bottomed pot over medium-high heat, heat the oil until shimmering. Pat the chicken dry and season lightly all over with salt and pepper. Working in batches, add the chicken, skin side down, to the pot. Sear, turning once, until golden brown on both sides, 10 to 12 minutes total; transfer the chicken to a plate.
Step 3
Decrease the heat to medium and add a drizzle of oil if the bottom of the pot looks dry. Add half of the roasted peppers, the garlic, and red pepper flakes, if using, and cook, stirring occasionally, until the garlic is tender and fragrant, about 2 minutes. Stir in the wine and let cook down by about half, 1 to 2 minutes.
Step 4
Meanwhile, put the tomatoes, with their juices, in the same bowl you used for the peppers and gently break them up into small pieces. Add the tomatoes with their juices to the pot, along with the 1/4 teaspoon salt and a generous amount of black pepper.
Step 5
Nestle the chicken pieces in the sauce, spooning some of it over the top. Increase the heat to medium-high and bring to a boil, then reduce the heat to medium-low, cover, and cook, stirring occasionally, until the chicken is tender, about 45 minutes.
Step 6
Uncover, increase the heat to medium-high, and cook at a lively simmer, stirring often, until the sauce thickens a bit, about 10 minutes, adjusting the heat as needed.
Step 7
Stir in the remaining pepper strips, taste, and season with more salt, if desired.
Step 8
Serve hot, generously sprinkled with chopped basil.