Chocolate Cherry Olive Chili

“You mean chocolate, cherries, and olives all mixed together... with beef?” Yes! It sounds ridiculous, but I promise you this Cuban style chili is ridiculously good. Just ask all of the chili cookoff competitors who lost to this recipe. It’s fine to just use the Chili sauce, olives, and cherries with your preferred cooking style for the meat (ie BBQ), substituting chicken or pork for the beef.

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Servings: 8

Prep Time: 00:45

Cook Time: 12:00

Chili Sauce

1 tablespoon olive oil

4 large cloves garlic, minced

3 cups water

1 28 ounce can crushed tomatoes

1/4 cup apple cider vinegar

1/4 cup brown sugar

1 tablespoon chili powder

2 tablespoons cayenne pepper sauce

2 teaspoons cumin

3/4 teaspoon cinnamon

1/2 teaspoon allspice

1 ounce 100% cocoa chocolate


2 tablespoons vegetable oil

4 pounds chuck roast (or your favorite cut of meat)

1 16 ounce can crushed tomatoes

1 tablespoon kosher salt

1 tablespoon crushed black pepper

1 cup green olives, with pimentos, chopped

1 cup dried cherries, chopped


1Evenly rub the chuck roast (or your preferred cut of meat) with salt and pepper.

2In a large stainless steel or cast iron skillet heat the vegetable oil over medium-high heat. Add the chuck roast to the skillet and sear each side of the cut of meat. You want to thoroughly brown each side of the meat, to the point of being almost crispy, about 4 to 5 minutes per side.

3After you have seared all sides of the roast, place the meat in a slow cooker (crock pot) and pour the 16 ounce can of crushed tomatoes over the meat. Cook with low heat for 8 to 10 hours, depending on the thickness of your cut of meat.

4In a large saucepan (or medium sized pot), heat the olive oil over medium heat, then add garlic. Cook garlic for about 1 and half minutes, or until garlic begins to brown slightly. Then reduce heat before next step.

5Add the 28 ounce can of crushed tomatoes and water to the saucepan. Be very careful of the oil splattering (which is why you should reduce the heat before adding the liquid to oil).

6Except for the chocolate, add the remaining chili sauce ingredients to the saucepan. Bring to a boil, then reduce heat and simmer uncovered for about 30 minutes. Simmer and stir often, until the sauce is reduced by about a third.

7Add the 1 ounce of chocolate to the sauce, stirring the chocolate into the sauce as it melts. Then remove the sauce from the heat and transfer to a glass bowl and refrigerate until the slow cooking meat is ready.

8After the slow cooked meat is done cooking, discard the fat and crushed tomatoes the meat was cooking in. Chop or shred the meat into bite size pieces or cubes, removing any excess fat.

9Return the meat to the slow cooker, then add the olives and cherries to the slow cooker as well. Mix the olives and cherries into the meat. Add the chili sauce to the slow cooker, thoroughly mixing all ingredients.

10Set the slow cooker to high heat to bring your chili up to serving temperature, then reduce the heat to low heat and serve.

Additional Notes

Like all chilis, this will benefit from sitting in the fridge for a day before serving. Also, this goes well with black beans and rice.

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