Combine tomatoes, onion, celery, carrot, tomato paste, steak sauce, bell peppers, wine, and red pepper flakes in a large pot. Bring to a simmer over medium-low heat.

While tomato mixture simmers, cook bacon in a large skillet over medium-high heat, turning occasionally, until evenly browned, about 10 minutes. Drain bacon slices on paper towels.

Cook and stir beef in bacon drippings over medium-high heat until brown and crumbly; drain. Stir in chili seasoning.

Stir seasoned beef, bacon, and cumin into tomato mixture. Continue to simmer until vegetables are tender and flavors are well blended.