For the chimichurri sauce, finely mince garlic, cilantro, and parsley. Add to a small bowl and stir in the oil, vinegar, oregano, salt, and crushed red pepper flakes. You can also chop in a blender by gently pulsing.
For the horseradish sauce, combine all ingredients in a small bowl and mix until combined. Can be made a day ahead and stored covered in the fridge.
Preheat the oven to 415°F. Remove the steak from the fridge 30 minutes prior to cooking. This is to bring the steak to room temperature and ensure your cooking times are more accurate. Season all sides liberally with salt and pepper. This can be done while your steak comes to room temp.
Add 1-2 tablespoons of oil to an oven-safe cast iron skillet and turn the heat up high, allowing the skillet to become very hot. Twirl the pan to distribute oil as it heats. Once the oil starts to smoke, place the porterhouse face down and sear undisturbed for 2 minutes. Flip the steak and sear for an additional 2 minutes. This will give your steak a nice seared edge.
Transfer your skillet directly to the oven. [WARNING] The skillet may be hot, handle it with oven mitts. For rare, bake for 4 minutes. Medium rare, 5-6 minutes. Medium, 6-7 minutes. Medium well, 8-9 minutes. Remember, depending on the size of the steak, the more or less time it will take. This recipe is ideal for a 32-ounce porterhouse, roughly 1.5-2 inches thick.
Remove steak from the skillet and place on a cutting board to rest for 10 minutes as you prepare the au poivre sauce.
For the au poivre sauce, return the same skillet, with the pan drippings, to the stove over medium-low heat. Melt butter and add the shallots and peppercorns (as coarse as possible). Cook until shallots start to soften, about 2-3 minutes. Stir occasionally to prevent burning. Add the cognac and cook until mostly evaporated, about 2 minutes.
Add cream and bring to a simmer. Cook until thickened enough to coat the back of a spoon. About 1 minute.
Slice the porterhouse into 1-inch thick strips, separating from the bone. Serve with au poivre, chimichurri, and horseradish sauce.