Pre-heat oven to 350°F.
Rub the chicken breasts all over with about 1 tbsp of oil, and season with about 1 tsp salt, 1 tsp pepper, and 1 tsp Cajun seasoning. Place on a rimmed baking sheet lined with a baking rack. Roast in the oven for 50 minutes, or until an instant-read thermometer reaches 165°F when inserted into the thickest part of the breast. Remove and let cool. Remove the skin and then pull the meat from the bone and cut into 1-inch pieces. Set aside.
In a large, heavy skillet, heat 1 cup of the oil over medium heat. Add the flour and use a whisk to fully incorporate.
Bring the mixture to a strong simmer, and then lower the heat to low. Whisk constantly until the roux has turned a dark brown color, about 30 to 40 minutes. Don't let the roux burn! If black specks appear, discard the mixture and start again. Transfer to a heat-proof bowl to cool.
In a medium saucepan, heat about 1 tsp of oil over medium heat. Cook the sliced sausage until slightly browned, about 5 minutes. Set aside.
In the same skillet, over medium heat, add the okra and cook until no longer slimy and slightly browned, about 5 minutes. Set aside.
In a large soup pot, or Dutch oven, heat the butter over medium heat. Add the onion, celery, bell pepper, poblano, jalapeno and sauté until soft and translucent, about 4 to 8 minutes. Add the garlic and cook for another 1 minute.
Add salt (1 tsp), black pepper (1 tsp), white pepper (1 tsp), chili powder (1 tsp), smoked paprika (1 tsp), and filé powder (1 tsp) to the vegetables. Stir and cook for 1 to 2 minutes.
Add the stock and bring to a boil. Lower the heat to medium and simmer for 15 minutes.
Add 1 cup of the dark roux into the pot and stir to incorporate.
Add the chicken and simmer for 30 minutes. Skimming oil from the surface when visible.
Add the sausage and simmer for another 30 minutes, continuing to skim excess oil.
In the last 5 minutes, add the sauteed okra.
Taste and add salt, if necessary.
Serve over steamed white rice and cayenne hot sauce. Garnish with sliced scallions, if desired.
