Preheat oven to 450°
Place steaks on a plate, season with salt, pepper, and rosemary. Add a drizzle of Worcestershire and let rest.
Dice the potatoes, and add to a bowl. Mix with a healthy drizzle of olive oil, and season generously with chili powder, garlic powder, rosemary, and salt and pepper. Can add cayenne pepper for heat. Spread evenly in a baking dish, and bake at 450° for 22-25 minutes stirring once in middle. Looking for crispy and golden brown skins.
While potatoes cook, very finely chop the white onion, trim butt ends of asparagus and discard, finely mince garlic. After flipping potatoes, preheat cast iron skillet on the stove, high heat, add healthy drizzle of olive oil coating the bottom of pan.
When pan is hot, add steaks and do not touch, letting sear for about 2.5-3 minutes. Mirror the sear on both sides, looking for a nice even brown color on bottom of steak while still red in the middle. Hopefully at this time the potatoes should be out of the oven, if not no worries, let them crisp up while moving on to next step. Remove potatoes when done, and cover to keep warm.
Lower the heat in oven to 400 and add the cast iron skillet with the steaks, it is okay to add the steak as it is cooling down. Bake for 6-10 minutes depending on desired doneness. Pull the steaks out, remove from pan, cover and let rest on a plate saving juices in skillet.
Return the cast iron skillet to low heat, add finely chopped onions and a couple pads of butter. When onions are translucent, add minced garlic, another drizzle of Worcestershire sauce, beef broth and red wine. Let simmer, stirring occasionally, allowing to reduce add salt and pepper to taste. Remove when reduced a little more than half, think slightly watery gravy, and place in serving dish.
While sauce reduces, heat another large skillet over medium heal, add a drizzle of olive oil. Add asparagus, and flatten out on the plan spreading out for best surface area and allow to sit for about 2 minutes, then flip trying to keep the asparagus lined up together and flat. Season with salt and pepper, and squeeze a slice of lemon or two over the asparagus. Continue to cook, flipping occasionally until desired tenderness, typically about 6 minutes.