Preheat oven to 325°F (165°C). Season beef chuck roast with salt and pepper.
In a large oven-safe pot, heat oil over medium-high heat and sear the roast on all sides until browned.
If using, pour in red wine and let simmer until reduced by half. Add mushrooms, onion, and garlic, then beef stock. Season with salt and pepper.
Cover and place in the oven to cook for 3 to 4 hours until beef is tender.
Once cooked, remove beef and let it rest. Strain cooking liquid and measure out 2 cups of broth.
For gravy, mix corn starch with cold water to create a slurry. Whisk into the simmering broth until thickened.
Prepare mashed potatoes by boiling cubed potatoes until tender. Drain, return to pot, add milk and butter, and mash until creamy.
Slice or shred the roast beef. Toast slices of white bread to serve as the base. Assemble by placing mashed potatoes on bread, topping with beef, and pouring gravy over.
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Notes
Beef Manhattan is best served hot and can be customized with various sides.