If spooning chimichurri over a pan-seared steak is a new experience for you, prepare for a revelation. Popular in Argentina and Uruguay, the combination of olive oil, parsley, garlic, and a splash of vinegar is a fresh, tart complement to this tender steak. You'll also want to dip the crispy oven-roasted potatoes and tomatoes in it. It would even work wonders on shoe leather, but let's hope it doesn't come to that.
Halve potatoes, then cut each half into four wedges. Place wedges on prepared baking sheet and toss with 1 Tbsp. olive oil, ½ tsp. salt, and ¼ tsp. pepper. Spread into a single layer and roast until potatoes are tender and golden brown, 20-25 minutes. Potatoes will finish cooking in a later step. While potatoes roast, prepare ingredients.
Prepare the Ingredients
Stem parsley. Mince stems and finely chop leaves. Mince garlic. Halve tomatoes lengthwise. Pat steaks dry, and season both sides with ¼ tsp. salt and a pinch of pepper.
Make the Chimichurri
Combine parsley leaves and stems, red wine vinegar, garlic (to taste), red pepper flakes (to taste), dried oregano, 2 Tbsp. olive oil, 1 Tbsp. water, and ¼ tsp. salt in a mixing bowl. Stir together and set aside to allow flavors to marry.
Cook the Tomatoes
Heat 1 tsp. olive oil in a medium non-stick pan over medium-high heat. Add tomatoes to hot pan, cut side down. Sear until browned, 2 minutes. Remove from pan. After potatoes have roasted 20-25 minutes, add tomatoes to baking sheet, seared side up. Bake until tomatoes are softened, but not mushy, 3-4 minutes. Remove from oven and set aside. Wipe pan clean and reserve.
Cook the Steaks
Return pan used to cook tomatoes to medium-high heat. Add 1 tsp. olive oil and steaks to hot pan. Sear undisturbed until browned, 3-4 minutes. Flip steaks, reduce heat to medium, and cook until steaks reach a minimum internal temperature of 145 degrees, 4-6 minutes. Remove steaks from pan and rest 5 minutes.
Plate the Dish
Serve potatoes on a plate and place tomatoes next to them. Slice steak into ¼" slices, if preferred. Serve steak up against potatoes and top with a spoonful of chimichurri. Serve remaining chimichurri on the side for dipping.