4 tablespoons extra-virgin olive oil, divided
2 pounds stewing beef
1 tablespoon salt, plus 1 teaspoon
1/2 teaspoon black pepper
3 carrots, peeled and medium dice
1 onion, small dice
2 stalks celery, medium dice
2 tablespoons all-purpose flour
2 cups dry red wine
1 ½ cups beef stock
2 pounds Yukon gold potatoes, peeled and quartered
3/4 cup milk
3 tablespoons butter
Preheat oven to 325 F. Grease a 2-quart baking dish with 1 tablespoon olive oil.
Pat stewing beef dry with paper towels.
Heat remaining 3 tablespoons olive oil in a Dutch oven set over medium-high heat.
Add beef to the Dutch oven in batches, making sure not to overcrowd the pan. Season with salt and pepper.
Sear the meat for 2 to 3 minutes per side until brown. Remove from the Dutch oven, and repeat with remaining batches.
Remove all meat from the pan, and turn heat down to medium.
Add carrots, onion and celery to the Dutch oven.
Turn to coat in fat, and cook for about 5 minutes, until vegetables have started to soften.
Add flour to the pan, and whisk into the remaining fat. Cook for 2 minutes.
Slowly add red wine, whisking to prevent lumps.
Add beef stock to the pan, and turn heat to medium-high.
Bring liquid to a boil, and cook for 2 minutes to thicken.
Add beef back to the Dutch oven, and stir.
Place the Dutch oven into the preheated oven. Cook for 2 to 3 hours, until the meat is very tender.
As the meat is cooking, place potatoes in a large pot, and fill to cover with 2 inches of water. Season water with 1 tablespoon salt and stir.
Place potatoes over high heat and bring to a boil. Cook for 20 minutes, or until potatoes can be pierced easily with a fork.
Drain potatoes, and add back to empty pot. Add milk and butter, and mash using a potato masher.
When the meat is finished cooking, remove from the oven, and increase heat to 375 F.
Shred the meat, still in the red wine gravy, using two forks.
Spoon beef and vegetables into bottom of the 2-quart baking dish.
Spoon potatoes over top of the beef mixture.
Place the baking dish onto a baking sheet to catch drips.
Place the baking sheet in the oven. Bake for 20 to 30 minutes until the entire dish is hot and bubbling throughout, and the potatoes have browned slightly.
