Step 1

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.

Step 2

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.

Step 3

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.

Step 4

Serve chili topped with queso fresco, cilantro, and drained pickled onion.