Homemade oxtail chili featuring black beans, pinto beans, and dark chocolate simmered in an oxtail and red wine demi-glace. Oxtail chili is smothered over crispy french fries and topped with cheddar, jalapeños, and a sunny-side-up egg. Don’t forget the spicy mayo sauce for an extra kick!
Season oxtails with salt and pepper. Place oxtails in a slow cooker, cover with water, and slow cook for 8 hours. After 8 hours, reserve at least 4 cups of braised water for demi-glace and chili. Pull oxtail meat off the bone and place it in a bowl, cover it, and transfer it to the refrigerator until ready to use.
Prepare demi-glace by combining 2 cups of reserved stock from slow cooking the oxtail, pinot noir, onion, thyme, peppercorns, bay leaf, and butter in a pot over medium-high heat.
Bring the mixture to a boil. Then reduce and simmer, covered for two hours. Stir occasionally.
Heat neutral oil in a separate large pot over medium high heat. Add onions and bacon, and sauté until onion is translucent, about 5 minutes.
Add jalapeños, brown sugar, smoked paprika, chili powder, granulated garlic, granulated onion, black pepper, oregano, cumin, and mustard powder. Stir to combine.
Stir in tomato sauce and chili paste.
Pour in 2 additional cups of reserved oxtail broth, stout, and chicken broth.
Add dark chocolate chips, Worcestershire, red wine vinegar, pinto beans, and black beans.
Mix in the prepared demi-glace and the pulled oxtail meat.
Add salt and pepper and continue cooking until liquid cooks down and chili thickens, about 2 hours. Stir occasionally.
Meanwhile, prepare the Spicy Mayo. Mix ½ cup mayonnaise with cayenne pepper puree. Refrigerate until ready to use.
Smother the oxtail chili on top of french fries and sprinkle with cheese. Drizzle with spicy mayo and top with sliced jalapeños and a sunny-side-up-egg.