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Combine the granulated garlic, granulated onion, crushed red pepper, sugar, 3 tablespoons salt and 2 tablespoons black pepper in a small bowl. Rub the pork shoulder with the olive oil and then with the seasoning blend.
Place the pork in a deep dish, such as a Dutch oven, and cook, uncovered, until an instant-read thermometer reads 190 degrees F., about 2 hours. (The rule of thumb when it comes to pork shoulder is 1 hour of cooking time for every pound. It might take a bit longer, but be patient.) When finished, the meat should pull apart easily. Shred and set aside.
For the gumbo: While pork is in the oven, start your roux by heating the canola oil in a stockpot on low heat. When the oil is hot, stir in the flour. Cook slowly until the roux turns a dark brown, about 2 to 3 hours.
Add the onion, bell pepper and celery and sweat in the roux, about 10 to 15 minutes. Add the okra, Cajun spice, Worcestershire sauce, garlic powder, gumbo file, onion powder, andouille and bay leaves and cook 2 minutes. Add the tomatoes and chicken stock and continue to cook on low heat, stirring occasionally, about 2 hours. Remove the bay leaves and stir in the pulled pork. Serve hot with cooked rice.
Special equipment: an instant-read thermometer