Step 1: In a large Dutch oven or heavy-bottomed pot, heat the olive oil over medium-high heat. Add the ground chuck and break it apart. Season with a generous pinch of kosher salt and black pepper. Brown the meat thoroughly, stirring occasionally, until no pink remains and it's nicely caramelized. Drain off any excess fat and set the browned meat aside.
Step 2: Reduce the heat to medium. Add the diced yellow onion and bell pepper to the pot. Sauté for 5-7 minutes, until softened, scraping up any browned bits from the bottom of the pot.
Step 3: Add the minced garlic, chili powder, ground cumin, smoked paprika, and dried oregano. Stir frequently for 1 minute until fragrant. Stir in the tomato paste and cook for another 2 minutes, stirring constantly to lightly toast it.
Step 4: Pour in the beef broth (or beer of choice) and bring to a simmer, scraping the bottom of the pot to deglaze and release any flavorful browned bits.
Step 5: Return the browned ground chuck to the pot. Add the fire-roasted diced tomatoes (undrained), tomato sauce, dark brown sugar, Worcestershire sauce, and bay leaf. Stir to combine.
Step 6: Bring the chili to a gentle simmer. Reduce the heat to low, cover, and cook for at least 30-45 minutes, stirring occasionally. For best flavor, simmer for 1-2 hours. The longer it simmers, the more the flavors will meld and deepen.
Step 7: Remove the bay leaf. Taste and adjust seasonings as needed, adding more salt, pepper, or a pinch of sugar if desired. Serve hot with your favorite toppings.