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Preheat the oven to 425ºF. In a large bowl, toss the Brussels sprouts with 2 tablespoons of olive oil and 1 teaspoon of salt. Spread them out into a single layer on a rimmed baking pan, cut side down. Cook for 20 minutes. Brussels should be browned in areas.
While the Brussels are roasting, cook the bacon in a large skillet (preferably cast iron) over medium heat, until tender and cooked through, about 10 minutes. (regulate the heat so the bacon doesn't get too crisp - you want it to cook slowly so it will be tender). Spoon out all but 2 tablespoons of fat from the skillet. Turn the heat down low. Add the cherries and cook, tossing, for 30 seconds or so, until they soften. Add the roasted Brussels to the skillet along with the remaining two tablespoons of olive oil and the balsamic vinegar (3 tablespoons). Cook, tossing, for 2-3 minutes to heat everything up and meld the flavors. Season with salt and pepper, to taste. Serve hot.