2 tablespoons vegetable oil, plus more as needed
4 ounces bacon, sliced crosswise into thin strips (1/4 -inch x 1-inch pieces)
2 pounds boneless beef chuck, trimmed, and cut into 1-inch cubes
Kosher salt and freshly ground black pepper, as needed
1 carrot, peeled and sliced into 1/4-inch-thick rounds
1 large yellow onion, medium diced
2 tablespoons unbleached all-purpose flour
1 1/4 cup full-bodied red Burgundy wine, divided
3 to 4 cups low-sodium beef broth
1 tablespoon tomato paste
2 large garlic cloves, minced
3 sprigs fresh thyme
2 bay leaves
2 tablespoons unsalted butter at room temperature
15 frozen pearl onions, thawed
8 ounces cremini or button mushrooms, trimmed and quartered
3 tablespoons chopped fresh flat-leaf parsley
1. Preheat oven to 325°F.
2. To a large Dutch oven over medium heat, add oil. When oil is shimmering, add bacon and sauté until lightly browned, about 5 minutes. Transfer bacon pieces with a slotted spoon to a bowl; reserve bacon fat in the pan.
3. Season beef with salt and pepper. Return Dutch oven to medium-high heat. When the fat is shimmering, working in batches to avoid crowding the pan, add beef and sear, turning as needed, until browned on all sides. Transfer to bowl with bacon. Add carrot and onion to the pan; sauté until lightly browned, about 8 minutes.
4. Return beef and bacon to the pan. Sprinkle flour over, then stir in tomato paste, garlic, thyme sprigs and bay leaves. Add 1 cup wine, then add enough broth just to cover the meat. Bring to a simmer over medium heat. Cover the pan and place in preheated oven for 1 1/2 to 2 hours until meat is fork tender.
5. Meanwhile, to a large skillet over medium-high heat, add butter. When butter is melted, add pearl onions and caramelize, about 3 minutes. Add mushrooms and cook until tender, about 5 minutes more. Drizzle with 1/4 cup wine and season generously with salt and pepper.
6. When the beef is fork tender, add the pearl onions and mushrooms to the Dutch oven. Taste and adjust seasoning with salt and pepper. Ladle into shallow soup bowls to serve.