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Step 1
Pound the chuck steaks to approximately 1/2" thick.
Step 2
Heat a large heavy pan to a touch higher than medium heat with 2 tablespoons of olive oil. Pat the steaks very dry and liberally season with salt and pepper on both sides. Sear the steaks in the hot pan until well browned on both sides then remove the steaks to a plate.
Step 3
Add the remaining olive oil to the pan along with the mushrooms and peppers. Saute until soft and brown (about 7-10 minutes) then add the garlic and cook for another 2 minutes or until lightly golden.
Step 4
Add the hot red pepper flakes and cook for another 30 seconds.
Step 5
Add the beef stock and wine and turn the heat to high for 2 minutes to cook off the alcohol. After 2 minutes reduce heat to medium-low and add the tomatoes to the pan and stir together. Bring the sauce to a lively simmer. Taste test and add salt and pepper to taste along with the dried oregano.
Step 6
Add the steaks to the pan and cover with the lid. Cook over a low simmer until very tender (90-120 minutes). Flip the steaks every 30 minutes to ensure even cooking. If the sauce starts to dry out during the braising process, just add a few ounces of water to the pan.
Step 7
Once the steaks are very tender, turn off the heat and taste test one more time, adjusting salt and pepper if required. There will be a good amount of fat in the sauce that has risen to the top. If you like, you can spoon it out, or use paper towels. Simply lay the paper towels on top of the sauce and lift. The fat will adhere to the paper towels. Repeat until the sauce looks
Step 8
Top with fresh basil and serve with grated Pecorino Romano and crusty bread to mop up the amazing sauce. Enjoy!