The beef chuck should be cut into half-inch cubes.
A large pot or Dutch oven should contain 3 tablespoons of oil. The oil should be heated on high.
The onion and garlic should be cooked for two minutes in the pot. The heat should be reduced to medium-high, then the beef cubes should be added. Make sure you stir the meat constantly while it is browning.
Immediately after the meat has browned slightly (without showing any red), lower the heat to medium.
In a large bowl, combine Italian seasonings, vinegar, smoked paprika, diced jalapenos, cumin, chili powder, tomatoes, beans, brown sugar, black pepper, salt, and red pepper flakes. Be sure to mix well.
Adding corn tortilla flour (or masa harina) will thicken the chili after simmering for about 10 minutes.
The chili should thicken after 10 more minutes of cooking.
Serve with your favorite sides.