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Add olive oil to a large, heavy-bottomed stockpot. Add onions and garlic and sauté until tender and translucent, about 10 minutes.
While onions are cooking, squeeze sausage out of its casings and crumble. Sauté meat in a 6-quart, or larger sauté pan until evenly browned.
Make a well in the center of the meat mixture. A golden liquid will quickly fill the well. Use a ladle to remove the fat to a large fat separator. Keep scooping until all the liquid is gone.
After juices settle to the bottom of the fat separator, pour them (about 2 cups) back into the stockpot. Discard fat that remains.
Prepare a mise en place for the remaining ingredients.
Add all ingredients except the olives to the meat and onion mixture. Rinse each can of tomatoes with ¼ cup of hot water and add that to the pot.
Simmer chili for 20 minutes on low heat stirring frequently.
Add coarsely chopped olives, stir, and cook for another 5 minutes.
Serve with bowls of garnish such as shredded cheddar cheese, sliced green onions, chopped parsley, and sour cream. Serve over rice, if desired.