Heat the olive oil in a large Dutch oven or heavy pot over medium-high heat. When it shimmers (but before it smokes), you're good to go.
Add the ground beef and break it apart with a wooden spoon. Season with a teaspoon of salt and half a teaspoon of pepper. Brown the meat thoroughly, about 6-8 minutes. Don't stir constantly – let it develop some crusty brown bits for maximum flavor. Those little crispy parts? Pure gold.
Using a slotted spoon, transfer the browned beef to a plate lined with paper towels. Leave about 2 tablespoons of fat in the pot (drain excess if there's too much).
Add the onions and bell peppers to the pot. Cook until softened, about 5 minutes. Your kitchen should start smelling amazing right about now.
Add the garlic and cook for another 30 seconds until fragrant. Don't let it burn – nobody wants bitter chili!
Time for the spice party! Add the chili powder, cumin, smoked paprika, oregano, cayenne, cinnamon, remaining salt, and pepper. Stir constantly for 1 minute until the spices are toasted and fragrant. This step blooms the spices and is non-negotiable for flavor depth.
Stir in the tomato paste and cook for 2 minutes, allowing it to caramelize slightly. It should darken in color – this develops a rich, umami base for your chili.
Return the browned beef to the pot and add the fire-roasted tomatoes (with their juice), all three types of beans, beef broth, brown sugar, Worcestershire sauce, and bay leaves.
Pour in the beer if using. (And maybe pour yourself one while you're at it. Cook's privilege!)
Bring everything to a boil, then reduce heat to maintain a gentle simmer. Partially cover the pot and let it work its magic for at least 30-45 minutes, stirring occasionally. The longer it simmers, the better it gets, honestly.
Taste and adjust seasoning as needed. If it's too thick, add a splash more broth. Too thin? Simmer uncovered for a few more minutes.
Remove bay leaves before serving. Ladle into bowls and let everyone customize with their favorite toppings. Watch the compliments roll in.