2 tablespoons olive oil, plus more as needed
3-4 pounds lean beef, trimmed of excess fat and cut into 2-inch cubes
kosher salt, to taste
2 tablespoons freshly ground black pepper, plus more for seasoning
4 cloves garlic, still in their peel and lightly smashed
1 2/3 cups Chianti or red wine, divided
3 cups beef stock
1 (14.5-ounce) can petite diced tomatoes
2 tablespoons tomato paste
2 teaspoons dried thyme
2 bay leaves
mashed potatoes, optional, for serving
green onions, chopped, optional, for garnish
In a 12-inch heavy-bottom pan with a tight-fitting lid, heat the olive oil.
Season the beef cubes with salt and pepper.
Add about 1/3 of the beef cubes to the hot oil in the pan. Let the beef sear undisturbed for about 3 minutes.
Add in the cloves of garlic.
Turn the beef cubes and sear on the other side for about 3 minutes.
Transfer the seared beef to a plate.
Repeat the searing process in 2 more batches.
Once all the beef is seared, return the beef to the pan over high heat.
Add 1 cup of Chianti to the pan. Let the wine boil, scraping the bottom of the pan to incorporate browned bits at the bottom, until reduced slightly, about 2 minutes.
Add the beef stock, petite diced tomatoes, and tomato paste to the pan, stirring to combine.
Add the dried thyme and bay leaves into the sauce.
Bring the sauce to a boil.
Once the sauce is boiling, cover the pan with the lid, reduce the heat to its lowest setting, and let the mixture simmer until the beef is tender, for 2 hours.
Remove the lid and stir in the remaining 2/3 cup Chianti and 2 tablespoons black pepper.
Increase the heat to medium and let the mixture simmer uncovered until the sauce is thick and deep mahogany in color, about 20-30 minutes.
Remove the garlic peels and bay leaves.
Serve over mashed potatoes.