Heat 1 tablespoon of olive oil in a large skillet over medium heat. Sear the seasoned chicken for about 3-4 minutes per side until golden brown. Transfer the chicken to a plate.
Add the whole peeled tomatoes. Use a spoon to gently crush them into uneven pieces. Stir in the red pepper flakes, Kalamata olives, capers, and the remaining dried oregano.
Return the chicken to the skillet, nestling it into the sauce. Cover and simmer for about 10 minutes until the chicken reaches an internal temperature of 165°F.