Preheat the oven to 350 degrees F (175 degrees C).

Cook bacon in a large oven-safe or cast-iron skillet over medium-high heat, turning occasionally, until evenly browned, about 10 minutes. Drain on a paper towel-lined plate until cool; crumble bacon. Leave drippings in the skillet.

Whisk flour, 1/2 teaspoon kosher salt, and smoked paprika together in a medium bowl until evenly combined; dredge chicken thighs in flour and shake off excess.

Cook chicken in drippings in the skillet over medium heat until browned, about 5 minutes per side; transfer chicken to a plate.

Drain and discard all but 1 tablespoon drippings from the skillet. Add onion and apple; cook and stir until onion is translucent and apple softened, about 5 minutes. Stir in cabbage and bacon; season with kosher salt. Cook, stirring often, until cabbage is softened, 5 to 8 minutes.

Add vinegar and red wine to cabbage mixture; stir in brown sugar and cinnamon until well combined. Bring to a boil; cook until sauce is reduced by half, stirring often, about 10 minutes. Place chicken thighs on cabbage in the skillet.

Bake in the preheated oven until cabbage is tender and chicken is cooked through, about 40 minutes. An instant-read thermometer inserted into the thickest part of a thigh should read at least 165 degrees F (74 degrees C).