Preheat oven to 375 degrees. Heat oil in a large braiser or straight-sided ovenproof skillet over medium-high. Season chicken with salt and pepper; cook, skin-sides down, until golden brown, 5 to 6 minutes. Turn and brown on other sides, about 2 minutes. Transfer to a plate.

Pour off all but 2 tablespoons fat from skillet. Reduce heat to medium; add onion and garlic and cook, stirring, until onion is translucent, about 3 minutes. Stir in freekeh and cook about 30 seconds. Stir in 1 cup water, 1/2 teaspoon salt, and thyme. Return chicken to pan; add tomatoes and olives. Bring liquid to a boil, then cover and roast in oven until freekeh is tender and chicken is cooked through, about 30 minutes. Let stand 15 minutes; serve.

Preheat oven to 375 degrees. Heat oil in a large braiser or straight-sided ovenproof skillet over medium-high. Season chicken with salt and pepper; cook, skin-sides down, until golden brown, 5 to 6 minutes. Turn and brown on other sides, about 2 minutes. Transfer to a plate.

Pour off all but 2 tablespoons fat from skillet. Reduce heat to medium; add onion and garlic and cook, stirring, until onion is translucent, about 3 minutes. Stir in freekeh and cook about 30 seconds. Stir in 1 cup water, 1/2 teaspoon salt, and thyme. Return chicken to pan; add tomatoes and olives. Bring liquid to a boil, then cover and roast in oven until freekeh is tender and chicken is cooked through, about 30 minutes. Let stand 15 minutes; serve.