In a large bowl, cover sauerkraut with water. Heat a large Dutch oven or other heavy pot over medium-high. Season chicken with salt and pepper. Add to pot, skin side down, and cook, turning until browned on all sides, 8 minutes. Transfer chicken to a plate. Add kielbasa, cut side down, to pot and cook until browned on both sides, about 4 minutes, flipping once. Add carrots, onion, and 1/2 cup water; cook, stirring and scraping up browned bits with a wooden spoon, until water is evaporated and onion is softened, 6 to 8 minutes. Add wine and bring to a boil.
Drain sauerkraut, pressing to remove as much liquid as possible. Add to pot, along with sugar, bay leaves, and caraway seeds; season with salt and pepper. Stir to combine.
Place chicken, skin side up, on top of sauerkraut and bring mixture to a boil. Reduce heat, partially cover pot, and rapidly simmer until chicken is cooked through and liquid is slightly reduced, about 20 minutes. Remove bay leaves before serving.
Flavor Tips: Soaking and then simmering the sauerkraut mellows its sharp bite but leaves enough zip to complement the sausages and chicken. For a spicy kick, try andouille sausage instead of kielbasa.
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