Step 1
Preheat the oven to 400°F. In a small saucepan, add the acorn squash along with enough water to cover it and a pinch of salt. Bring it to a gentle simmer and cook until the squash is tender. Once softened, strain the squash and transfer it to a blender—or return it to the pot if using an immersion blender. Add the butter and heavy cream, then blend until completely smooth. Season with salt and pepper to taste, and keep the purée warm on the stove over low heat until ready to serve.
Step 2
In a small bowl, combine the olive oil, white wine vinegar, minced garlic, oregano, red pepper flakes, and finely chopped parsley. Stir well to combine and season with salt to taste. Let the chimichurri sit at room temperature to allow the flavors to develop; do not refrigerate, as this will intensify its taste.
Step 3
Trim the woody ends off the asparagus, removing about 1 inch from the base. Lightly score around the lower part of each stalk, then use a paring knife to peel away the tough outer layer up to the score line. Place the prepared asparagus in a small roasting pan, drizzle with olive oil, and season generously with salt and pepper. Toss to coat evenly, then transfer to the oven to roast for about 20 minutes, until tender and slightly caramelized.
Step 4
Heat a cast iron pan over medium-high heat and drizzle with olive oil. Generously season the NY strip steak with salt, pepper, and a pinch of cayenne for added depth. Sprinkle the steak with brown sugar, rubbing it evenly across the surface, then finish by coating it with a fine dusting of ground coffee. Once the pan is hot, place the steak in to sear for about five minutes on one side. Use tongs to hold the steak upright and sear the fat side to render it before flipping to cook the other side. After flipping, add butter, whole cloves of garlic, and fresh rosemary to the pan, basting the steak continuously for about six minutes or until it reaches medium-rare. Once cooked, remove the steak from the pan and place it on a small rack, pouring the basting liquid over the top. Allow it to rest for a few minutes before slicing. Meanwhile, return the pan to the heat and add thick slices of lemon, about 1 inch thick. Sprinkle them with salt and sear on both sides until lightly caramelized.
Step 5
By this point, the asparagus should be ready to come out of the oven, and it's time to plate. Slice the rested NY strip steak into pieces about 3/4 inch thick. On one side of the plate, place a generous spoonful of the acorn squash purée, using the back of the spoon to create an elegant swoosh across the plate. Neatly arrange about five pieces of steak on top of the purée. On the opposite side, carefully place five asparagus spears, then position the grilled lemon slice on top. To finish, lightly dress the micro arugula in a small bowl with a squeeze of lemon juice and a drizzle of olive oil, tossing gently to coat. Place the salad on top of the steak, then drizzle the chimichurri around the plate for both flavor and presentation. Serve immediately and enjoy.
