Heat the olive oil in a large, heavy-bottomed pot or Dutch oven over medium-high heat. Season the chuck roast generously with salt and pepper.
Sear the roast on all sides until browned, about 3–4 minutes per side. Remove the roast and set it aside.
Sauté the Vegetables:
In the same pot, add the sliced onion and garlic, cooking for 2–3 minutes until softened.
Add the chopped carrots and potatoes, and cook for another 3 minutes, stirring occasionally.
Cook the Pot Roast:
Return the roast to the pot and pour in the beef broth, red wine (if using), Worcestershire sauce, thyme, rosemary, and bay leaf. Bring the mixture to a simmer.
Cover the pot with a lid and reduce the heat to low. Let the roast cook for 3–4 hours, or until the roast is fork-tender and shreds easily.
Make the Mashed Potatoes:
While the roast is cooking, bring a pot of salted water to a boil. Add the peeled and chopped potatoes and cook until tender, about 15–20 minutes.
Drain the potatoes and return them to the pot. Add the butter, milk, salt, and pepper. Mash until smooth and creamy. Adjust the milk for your desired consistency.
Shred the Pot Roast:
Once the pot roast is tender, remove it from the pot and shred the meat using two forks. Discard the bay leaf.
Return the shredded roast to the pot with the vegetables and juices. Stir to combine.
Serve:
Serve the mashed potatoes on plates, and top with the shredded pot roast and vegetables. Spoon some of the rich gravy over the top for added flavor.
Serving and Storage Tips
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