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Trim fat from meat. Cut meat into 1/2-inch pieces. In a Dutch oven cook and stir meat, onion, and garlic in hot oil over medium-high heat until meat is brown. Stir in tomatoes, squash, kidney beans, black beans, corn, the water, chili powder, chocolate, cumin, cinnamon, and oregano.
Bring to boiling; reduce heat. Simmer, covered, about 30 minutes or until meat and squash are tender, stirring occasionally.