In a small bowl, whisk together 2 teaspoons chile powder, smoked paprika, 1 1/2 teaspoons salt, and 1/2 teaspoon black pepper. Season the chicken drumsticks and carefully loosen the skin to season the meat. Cover with plastic wrap and let marinate for at least 1 hour or overnight.
Meanwhile, add oil to a medium saucepan over medium heat. Once hot, add onion, and garlic, and saute until onion is soft and translucent. Add the remaining 1 teaspoon ancho chile powder, and tomato paste and toast for 1 minute. Add orange juice, lemon juice, ketchup, cherries, water, salt, and pepper. Reduce heat to low and simmer for 30 minutes. Puree with a hand blender until smooth. Reserve 1 cup sauce for grilling and hold the rest for serving.
Preheat a grill to medium heat. Oil the grill grate with olive oil to keep the chicken from sticking.
Grill chicken, turning frequently, until cooked through and skin is crisp, about 25 minutes. Brush with reserved barbecue sauce and grill 5 minutes more.
Serve the chicken with fresh cherries and a side of sauce.