Fire! Up! That! Grill!
½ cup extra-virgin olive oil, plus more for drizzlingPreheat oven to 350°. Remove stems and seeds from chiles and arrange on a small rimmed baking sheet. Cook until just barely dry and crisp, about 3 minutes . Let cool, then grind to a powder in a spice mill, mortar and pestle, or blender.
Whisk chile powder with garlic, vinegar, and ½ cup oil in a small bowl to combine; season with salt. Let sit while you grill the chicken. Prepare a grill for medium to medium-low heat. Working with 1 quarter at a time, place chicken, skin side down, on a cutting board. Using your fingers, feel for the thigh bone. Using a boning knife or another thin sharp knife, cut straight down into flesh until the tip of the knife hits the bone, then slice from one side to the other to expose its entire length.
Repeat this process, this time making a cut from the top of the drumstick bone down toward the foot end. Cut along either side of drumstick bone until you can wiggle your knife underneath. With the blade angled toward the cutting board this time, cut meat away from bone. By now the drumstick and thigh bones should be attached only where they meet at the joint. Make small cuts all around and underneath joint until you can cut out bones completely. Cut away any pieces of cartilage that remain.
Season chicken quarters on both sides with salt and pepper and drizzle with oil. Place on grill, skin side down, and close together, then place a sheet of foil over chicken, covering all of the pieces. Place a large cast-iron skillet on top to press down on chicken. Cook until skin is very crisp and chicken is 90% cooked through , 10–14 minutes . Turn chicken onto flesh side to finish cooking through, about 3 minutes longer.Chile oil can be made 3 days ahead. Let cool; cover and chill.
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