Cut the beef into large chunks and season generously. Heat 3-4 tablespoons of olive oil in a large pot over medium-high heat. Add the beef and braise until one side is well seared, then flip and sear the other side.

Once the beef is seared, add the chopped onions. Pour in 32 oz of beef bouillon along with the red wine. Reduce the heat to medium-low, cover, and let the beef simmer for about 2 hours, or until it begins to tenderize.

Meanwhile, chop the unpeeled potatoes into four equal pieces. Place them in a pot of water, add 1 teaspoon of salt, and bring to a boil. Cook until fork-tender. As the beef continues to cook, add 16 oz of beef stock, as the liquid will reduce during the long simmer process.

Chop the celery, carrots, Italian parsley, and garlic, and set aside. Once the beef is soft and tender (this can take up to 3 hours on the stovetop), add the vegetables and garlic to the pot. Stir, cover, and cook for an additional 30–35 minutes, until the vegetables are softened.

Drain the potatoes and mash them well. Add crushed garlic, butter, and milk, then mash until creamy and smooth. Serve the red wine–braised beef over the garlic mashed potatoes and enjoy.