Crisp the bacon: In a large pot or Dutch oven over medium heat, cook the diced bacon until browned and crisp, about 7–9 minutes. Use a slotted spoon to transfer bacon to a plate. Leave 1–2 tablespoons of the bacon fat in the pot and discard the rest.
Sauté aromatics: Add the diced onion and bell pepper to the pot.
Cook, stirring, until softened, about 4–5 minutes. Stir in the minced garlic and cook 30 seconds until fragrant.
Brown the beef: Add the ground beef, breaking it up with a spatula. Season lightly with salt and pepper.
Cook until no longer pink and most moisture evaporates, 6–8 minutes. If there’s excess grease, spoon off a bit, but leave some for flavor.
Build the chili base: Stir in tomato paste, chili powder, smoked paprika, cumin, onion powder, and garlic powder. Cook 1 minute to toast the spices.
Simmer: Add diced tomatoes, beef broth, Worcestershire (or aminos), and mustard.
Stir well, then bring to a gentle simmer. Reduce heat to low and cook uncovered for 20–25 minutes, stirring occasionally. The chili should thicken slightly.
Make it “cheeseburger” creamy: Stir in the cream cheese until it melts smoothly into the chili.
Add heavy cream and half of the shredded cheddar. Simmer on low 3–4 minutes, stirring, until melted and velvety.
Add bacon and pickles: Return most of the bacon to the pot (reserve some for topping). Stir in the diced pickles.
Taste and adjust salt and pepper. If you want it richer, add the remaining cheddar.
Serve: Ladle into bowls. Top with extra cheddar, bacon bits, green onions, jalapeños, and a few pickle pieces.
A drizzle of hot sauce is great if you like heat.