Heat 1 TBSP of the olive oil in a dutch oven or large pot over medium-high heat. Pat the chicken thighs dry with paper towels and lay HALF of the chicken thighs skin-side down in the pot and cook until the skin is browned, about 6 minutes. Transfer the seared chicken to a plate and set aside.
Brown the remaining chicken thighs in the dutch oven the same way then transfer them to the plate with the other chicken keeping any fat in the pot.
Reduce the heat to medium and add the remaining 3 TBSP of oil to the pot along with the flour, Cajun seasoning, 1/2 tsp salt, and 1/4 tsp black pepper. Stir until thoroughly combined scraping the bottom of the pan with a wooden spoon to release any stuck on bits of chicken skin. Continue stirring, constantly, until a dark brown roux is formed, about 15 minutes (Make sure you keep stirring during the entire 15 minutes to keep your roux from burning).
Add the onions, bell peppers, and celery to the pot and stir to combine. Cook, stirring often, until vegetables have softened just a bit, about 5 minutes.
Stir in the water and bay leaf and bring to a boil.
Return the chicken thighs to the pot then cover the pot and reduce the heat to medium-low. Simmer for 1 hour, stirring occasionally.
Transfer the chicken from the pot to a plate and shred the chicken off the bone using two forks. Discard the skin and bones and stir the shredded chicken back into the pot.
Simmer uncovered, stirring occasionally, about 90 more minutes or until thickened.
Season with additional salt and pepper to taste then serve the gumbo with steamed rice, green onions, and your favorite hot sauce.
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