This is hands-down a favorite dish to serve for friends and family. If you plan ahead, you can have this entire dish made the night before to let flavors meld, which makes your dinner party that much easier.
Preheat the oven to 350F with rack on lower middle position. Heat 2 TB oil in large Dutch oven (or heavy, oven-safe pot with tight fitting lid.) Add bacon and cook over medium until evenly and lightly browned throughout. Using a slotted spoon, remove bacon to a large plate. Remaining oil and grease should stay in the pot.
Using paper towels, thoroughly dry uncooked beef and sprinkle the cubes evenly with a thin layer of kosher salt and fresh ground pepper. Reheat the oil/bacon grease in the Dutch oven and sear the beef cubes in a single layer, working in batches, until each cube is brown on all sides. Do not over crowd the pan, making sure to leave some space between each piece of beef. Add more oil as needed to finish browning. Set beef aside in plate with the bacon.
If needed, heat 2 TB oil in pot. Add carrots, onions, garlic, 1 TB kosher salt, 2 tsp black pepper and sauté for 5 minutes until onions are lightly browned. Deglaze bottom of pot, adding 1 TB oil as needed. Add Cognac and cook another 10 minutes on medium.
Add beef and bacon back into Dutch oven with their juices. Add the wine and enough beef broth to almost cover all the meat. Add tomato paste, thyme, and bay leaves. Bring to simmer, stirring occasionally. Once liquid is reaches a simmer, cover the pot with tight fitting lid and place in oven for 1 1/2 to 2 hours, or until meat is very tender when pierced with fork.
Meanwhile, mix together 2 TB butter with 3 TB flour in small bowl and set aside. Sauté mushrooms with 2 TB butter in skillet just until mushrooms start to become soft.
Remove stew from oven. Add the butter/flour mixture, frozen pearl onions, and mushrooms to the stew. Bring to a boil on stovetop and immediately reduce to simmer. Cover and simmer for 30 minutes. Skim off any fat off the top. Remove bay leaves. Season with additional kosher salt and fresh pepper to taste. Garnish with fresh parsley and serve with crusty bread, rice, or egg noodles.
Notes
If not serving immediately, let the stew cool completely at room temperature and store in fridge. Just before serving, bring stew to a simmer. Cover and simmer 15 min, basting with its own sauce a few times while simmering.
If you cannot locate frozen whole pearl onions, you can replace with chopped sweet onions instead.
Wine Pairing: A good quality red, similar to the one you used in the recipe. A jammy Pinot Noir recommended.
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