Prepare the chicken: Whisk together the buttermilk, chile powders, paprika, coriander, garlic, onion powder and cinnamon in a large baking dish. Add the chicken and turn to coat. Cover and refrigerate at least 4 hours and up to 24 hours, turning a few more times. Remove the chicken from the brine and pat dry with paper towels. Put the chicken on a baking rack set over a baking sheet. Return to the refrigerator and let sit, uncovered, at least 1 hour and up to 4 hours.
Meanwhile, make the glaze: Heat the oil in a large saute pan over medium-high heat. Add the onion and cook until soft, about 4 minutes. Add the garlic and cook 1 minute. Add the mangoes and cook, stirring occasionally, until broken down and caramelized, about 10 minutes. Add the white wine and cook until reduced by half, about 2 minutes. Carefully transfer the glaze mixture to a blender; add the pineapple juice, orange juice and the chile de arbol powder and blend until smooth, about 2 minutes. Strain into a bowl and season with the honey and salt and pepper. The mixture should be a thick puree. If it is too thick, thin it with a touch of water. Let cool to room temperature before serving.
Grill the chicken: Heat your grill to medium for indirect grilling. Remove the chicken from the refrigerator 30 minutes before cooking. Brush the chicken on both sides with the oil; season with salt and pepper. Put the chicken, skin-side down, on the hotter side of the grill (direct heat) and grill until browned, 4 to 5 minutes. Turn the chicken and continue grilling until the bottom is golden brown, 4 to 5 minutes. Move to the cooler side of the grill (indirect heat), close the cover and continue grilling until an instant-read thermometer inserted into the thickest part of the breast (not touching the bone) registers 160 degrees F, 15 to 20 more minutes. During the last few minutes, brush with some of the glaze. Remove the chicken to a platter and drizzle with more of the glaze. Tent loosely with foil and let rest 10 minutes before serving.
Photograph by Jennifer Causey
Recipe courtesy of Bobby Flay for Food Network Magazine