Heat 1 tablespoon oil in a large Dutch oven over medium-high heat and brown the beef chuck cubes on all sides, about 8 minutes. Remove and set aside.
In the same pot, brown the sliced sausage until caramelized, about 5 minutes. Remove and set aside with the beef.
Add remaining oil to the pot and sauté the onion until softened, about 5 minutes. Add garlic and cook for 1 minute until fragrant.
Stir in chili powder, smoked paprika, cumin, and oregano, cooking for 1 minute to toast the spices.
Add the diced tomatoes, tomato paste, beef broth, salt, and pepper. Return the beef and sausage to the pot and bring to a boil.
Reduce heat to low, cover, and simmer for 2 hours, stirring occasionally, until the beef is very tender.
Add the pinto beans and simmer uncovered for an additional 30 minutes to thicken the chili.
Taste and adjust seasoning as needed before serving with your favorite toppings.