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Thick, meaty Short Rib Chili gets layers of heat from fresh jalapeños, smoky chipotles in adobo, and fruity ancho chile powder. Tender short ribs in chili are delicious, but feel free to substitute cubed beef chuck roast for a more economical option.
Heat oil in a large enameled Dutch oven over medium-high. Toss together beef, 4 teaspoons salt, and 2 teaspoons black pepper in a large bowl. Working in 3 batches, add beef to hot oil and cook, turning occasionally, until browned on all sides, 8 to 10 minutes per batch. Using a slotted spoon, transfer beef to a medium bowl.
Add chopped onion, jalapeños, garlic, remaining 1 teaspoon salt, and remaining 1/2 teaspoon black pepper to drippings in Dutch oven. Cook over medium, stirring occasionally, until onion is softened and lightly browned, about 8 minutes. Stir in tomato paste, chile powder, chipotles, oregano, cumin, and coriander; cook, stirring constantly, until mixture is fragrant and vegetables are evenly coated, 1 to 2 minutes. Add wine; cook, scraping up browned bits from bottom of Dutch oven, until liquid is slightly reduced, about 2 minutes. Add crushed tomatoes and broth; bring mixture to a simmer over medium-high. Stir in beef and any juices in bowl. Reduce heat to low; cover and simmer, stirring occasionally, until beef is very tender, 2 hours and 30 minutes to 3 hours, uncovering during final 30 minutes of cook time. Season with additional salt and black pepper to taste.
While chili cooks, place sliced red onion in a medium-size heatproof bowl; set aside. Combine vinegar, 1 cup water, sugar, and salt in a small saucepan. Bring to a boil over medium-high, stirring often to dissolve sugar. Pour hot vinegar mixture over onion, pressing onion pieces with a spoon to keep submerged. Let stand at room temperature 10 minutes. Cover and chill at least 1 hour or up to 3 days.
Serve chili topped with queso fresco, cilantro, and drained pickled onion.