Preheat & dry the chicken.
Preheat your oven to 350 °F (≈175 °C). Pat the chicken pieces dry with paper towels — moisture interferes with browning.
Season with 1 teaspoon kosher salt and ½ teaspoon black pepper. Let it rest 5 minutes.

Sear the chicken.
In a large 12‑inch oven‑safe sauté pan over medium heat, warm 1 tablespoon olive oil until shimmering.
Arrange the chicken skin‑side down in a single layer. Let it cook undisturbed until the skin is golden brown, about 12–15 minutes.
Flip the pieces and cook an additional 2 minutes.
Using tongs, transfer the chicken to a plate, skin‑side up (it won’t yet be fully cooked).

Sauté the vegetables and herbs.
Drizzle in the remaining tablespoon of olive oil into the pan. Toss in the sliced mushrooms, chopped parsley, oregano, thyme, plus the remaining ½ teaspoon salt and ¼ teaspoon pepper.
Stir frequently, scraping up browned bits from the pan bottom, until the mushrooms soften (≈2 minutes).

Cook shallot, garlic, and tomato paste.
Push the mushrooms outward, and in the center of the pan place the sliced shallot and garlic.
Let them soften and become fragrant for about 2 minutes.
Stir in the tomato paste, coating all ingredients, and cook for another minute to deepen flavor.

Deglaze and build the sauce.
Pour in the ½ cup white wine, stirring and letting it reduce by half (≈2 minutes).
Stir in the ½ cup chicken broth and increase heat to medium‑high; cook for about 2 minutes, stirring occasionally.
Add the canned whole peeled tomatoes (with juice), crushing them by hand as you do so.

Return chicken & bake.
Nestle the chicken back into the pan, skin‑side up, in a single layer. Bring the mixture to a boil, then transfer the pan to the oven.
Bake for 40 minutes to 1 hour, stirring every 20 minutes and scraping down edges to incorporate browned bits. The sauce should thicken and darken.

Finish & garnish.
Once cooked through and the sauce is deeply flavored, garnish with extra chopped parsley, oregano, and the optional sliced olives.
Serve hot over pasta, with crusty bread, or on its own.