The Tailgate Chili

The Tailgate Chili

So much chili so little time! The Whole30 Chili can be a bit…intense.  It has some real depth of flavor that is simply not everyone’s cup of tea.  For a more traditional tasting chili, we also fall back on our Tailgate Chili.  Which, as the name implies, is great for groups and a general people pleaser.  It does have some non-compliant options, so check your ingredients carefully if you are still on a Whole30.  Otherwise, let’s get cooking…or simmering!

This can be made ahead and reheated.

Tailgate Chili

Serves: 12

Prep Time: 30 min

Cook Time: 2 hours

Total Time: 2 ½ hours


  • 2 lbs. ground beef chuck
  • 1 lb. stew beef, diced
  • 4 slices of bacon
  • 2-28 oz. cans diced tomatoes with juice
  • 1-6 oz. can tomato paste
  • 1-15 oz. can pineapple, pureed
  • 1 large yellow onion, chopped
  • 3 stalks celery, chopped
  • 1 green bell pepper, seeded and chopped
  • 1 red bell pepper, seeded and chopped
  • 2 green chili peppers, seeded and chopped (jalapeno or poblano are good options)
  • 1/4 c. chili powder
  • 4-6 cloves garlic, minced
  • 1 Tbsp. dried oregano
  • 2 tsp. ground cumin
  • 1 tsp. dried basil
  • 1 tsp. salt
  • 1 tsp. ground black pepper
  • 1 tsp. cayenne pepper
  • 1 tsp. smoked paprika
  • 1 Tbsp. maple syrup (optional)
  • 1-12 oz. bottle dark beer (optional, replace with Beef Bone Broth or other compliant stock)


  • 1 bunch Cilantro, chopped
  • 2 Avocado, diced
  • 1 white onion, diced
  • Hot Sauce


Heat a large Dutch oven or stockpot over medium-high heat. Cook the bacon to crisp. Remove and cool. Do not drain off grease.

Crumble the ground chuck and stew beef into the hot pan, and cook until evenly browned. Drain off excess grease.

Pour in the diced tomatoes, tomato paste, and pineapple puree. Crumble the bacon and add to the pot. Add the onion, celery, green and red bell peppers, chili peppers, and beer or broth. Season with chili powder, garlic, oregano, cumin, basil, salt, pepper, cayenne, paprika, and syrup (optional). Stir to blend, then cover and simmer over low heat for at least 2 hours, stirring occasionally.

After 2 hours, taste, and adjust salt, pepper, and chili powder if necessary. The longer it simmers the deeper the flavors. Remove from heat and serve.

Serve with cilantro, diced onions, avocado, and hot sauce.

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