Heat 2 tablespoons olive oil in a heavy Dutch oven over high heat until shimmering. Add beef cubes in a single layer, working in batches if needed, and sear for 3 minutes per side until deeply browned. Transfer to a plate and set aside.
2 lbs beef chuck, 3 tbsp olive oil
Lower heat to medium and add remaining 1 tablespoon olive oil. Add pearl onions and cook for 15 minutes, stirring every 3-4 minutes, until golden and slightly softened. Remove and set aside with the beef.
1 lb pearl onions, 3 tbsp olive oil
Add tomato paste to the Dutch oven and cook for 2 to 3 minutes, stirring constantly to remove raw taste. Pour in red wine, scraping up all browned bits from the bottom. Add cinnamon sticks, whole cloves, bay leaves, and beef broth. Bring the mixture to a boil.
3 tbsp tomato paste, 1 cup red wine, 2 sticks cinnamon sticks, 5 whole cloves, 2 leaves bay leaves, 1 cup beef broth
Return the seared beef to the pot (leave onions out for now). Reduce heat to low, cover, and simmer gently for 2 hours. Add the caramelized onions and vinegar, then continue simmering uncovered for 30 more minutes until the beef is fork-tender and the sauce coats the back of a spoon.
2 lbs beef chuck, 1 lb pearl onions, 3 tbsp red wine vinegar
Remove from heat and let rest for 15 minutes. Pull out cinnamon sticks, cloves, and bay leaves before serving. The sauce will thicken slightly as it cools.
2 sticks cinnamon sticks, 5 whole cloves, 2 leaves bay leaves
