Heat 1 cup of canola oil in a small pan to 350°F. Cook the tortilla strips in batches until golden brown, about 1-2 minutes. Drain the tortillas strips on paper towels.
Add 2 tablespoons of oil to a Dutch Oven and heat over medium-heat until shimmering. Add the onion and cook until softened, about 5 minutes. Add the garlic and cook for another minute. Add the tomato paste and cook for 2 minutes. Remove from heat.
Add the cooked onions, garlic and tomato paste to a blender. Add the chipotle pepper, chili powder, cumin, oregano, paprika, ½ cup of water, ½ of chicken stock, ½ cup of fried tortilla strips and half of the canned tomatoes. Blend on high until smooth. Wipe out the Dutch oven and transfer the content of the blender to the Dutch oven.
Add the remaining chicken stock, Worcestershire sauce, corn, black beans and remaining fire-roasted tomatoes and bring to a boil. Reduce the heat to medium-low and cook for 45 minutes to blend the flavors.
Add the chicken and black olives and cook over medium-heat until chicken is warmed through, about 7 minutes. Season with salt and pepper to test.
Ladle the soup into bowls, garnish with cheese, cilantro and tortilla strips.