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Preheat the oven to 425°F.
Pat the chicken thighs dry and season them all over with salt and pepper.
Heat the oil in a Dutch oven or large oven-proof pot over medium-high heat.
Working in batches if necessary, add the thighs in a single layer and cook on one side until browned, 4 to 6 minutes.
Flip and let cook for another 1 to 2 minutes on the other side, then transfer to a plate and set aside.
Return the pot to medium-high heat and add the mirepoix blend and a pinch of salt.
Cook, stirring occasionally, until tender and browned, 3 to 5 minutes.
Add the rosemary, if using, and cook until fragrant, about 30 seconds.
Add the olive brine, scrape up any browned bits, and cook until the liquid has evaporated, about 1 minute.
Stir in the cherry tomatoes and olives and season with salt and pepper.
Remove the pot from heat and add the chicken, seared side up, and any juices back to the pot.
Cover the pot and transfer to the oven.
Bake until chicken is cooked through and registers 170°F to 175°F on an instant-read thermometer, about 15 minutes.
Serve the chicken topped with the tomato and olive mixture and some of the pan juices.