Sear-roast the chicken: Heat the oven to 425 degrees F. Turn the exhaust fan on to high. Pat chicken dry with paper towels. Season both sides generously with salt and pepper (about 1 teaspoon of each total). Heat a 12-inch heavy-based ovenproof skillet over medium-high heat until a droplet of water vaporizes in 1 or 2 seconds, about 1 minute. (If the water skitters around the pan and doesn't evaporate, the pan is too hot; take it off the heat for about 30 seconds to cool.)

Add the oil, swirl it around the pan, and then evenly space the chicken in the pan. Cook without touching for 2 minutes. Using tongs, lift a corner of the chicken, check that it's both well browned and easily releases from the pan, and flip it over. (If it sticks or isn't well browned, cook for 1 to 2 more minutes before flipping.) Cook the second side for 1 minute and then transfer the skillet to the oven.

Roast until the chicken reaches an internal temperature of 165 degrees F and is firm to the touch, about 5 to 8 minutes. Using potholders, carefully remove the pan from the oven, transfer the chicken to a large plate, tent with foil, and let it rest while you prepare the sauce in the same skillet.

Prepare the pan sauce: Pour off any excess fat from the skillet. Return the pan to high heat and add the red wine. Cook, scraping the pan with a wooden spoon to incorporate any browned bits, until the wine is reduced to a glazy film. Add the tomatoes with their juices and the red chile flakes; cook until the juices reduce to a saucy consistency, about 3 minutes. Stir in the oregano and Parmigiano; season generously with salt and pepper to taste. Serve immediately spooned over the sear-roasted chicken.

The flavor intensity brought out by searing, and the zippy flavors in the sauce, can handle a Chardonnay with some oak or a lighter Cotes du Rhone red.