Prep Chili: Bring a large cast iron skillet to medium-high heat. Add 1 tablespoon extra virgin olive oil and swirl to coat the pan. Add 1 tablespoon garlic and move around the pan for about 10-20 seconds. Add onions and allow them to cook down, about 2 minutes. Add 1 1/2 pounds ground beef to the pan, season with salt and pepper. Move around the pan (turn heat down a bit if you need to) until ground beef is no longer pink. Drain grease.
Slow Cooker: Add to crockpot along with 28 ounces canned whole tomatoes (use knife to cut them into quarters), 6 ounces canned tomato paste, 15 ounces canned red kidney beans, 1 bay leaf, 2 tablespoons chili powder, 1/2 teaspoon cumin, 1/2 teaspoon garlic powder, 1 teaspoon onion powder, 1 teaspoon kosher salt and 1/4 teaspoon ground black pepper. Stir to combine. Cook on the low setting of the slow cooker for 6-8 hours.
Prep Potatoes: During the last hour of the chili cooking - preheat oven to 350℉. Rinse 4 russet potatoes under cold water, pat dry with paper towel, and pierce each potato 3-4 times with a fork. Rub the outside of each potato with extra virgin olive oil and sprinkle with kosher salt.
Bake: Place the potatoes directly on the wire rack and bake for 60-75 minutes.
Cool + Cut: Carefully remove from oven, let cool slightly, and then use a sharp knife to make a cut, lengthwise, down the top of each potato.
Add Toppings: Scoop about a 1/2 cup of chili onto each potato, then some shredded cheese, to let it melt a little bit, and then add the rest of the toppings.