Look, I get it — skirt steak is one of those cuts that gives you maximum flavor for your dollar, usually running about $8-10/lb versus $15+ for ribeye. Two sauces means everyone's happy and you look fancy for basically the cost of herbs and mayo.
Make the chimichurri: Combine vinegar, lemon juice, parsley, oregano, and garlic in a blender and puree until smooth.
With the blender running, slowly drizzle in olive oil until the sauce comes together and emulsifies.
Stir in red pepper flakes. Transfer to an airtight container and refrigerate for up to 1 day. Bring to room temperature before serving.
Make the pineapple aioli: Mix mayo, drained pineapple, lime zest, and salt in a bowl. Cover and chill until ready to serve. (Use the cheapest mayo you can find — store brand works perfectly fine here since you're doctoring it up anyway.)
Preheat your grill to high heat.
Rub steaks with olive oil and season generously with salt and pepper. (Don't skip the salt — skirt steak needs aggressive seasoning to shine.)
Grill steaks 3-4 minutes per side for medium-rare to medium, or longer if you prefer them more done.
Let steaks rest for 5 minutes, then slice against the grain and serve with both sauces.
Cost breakdown: About $4.50 per serving including both sauces. The chimichurri keeps well and transforms any leftover protein. Buy pineapple in juice, not syrup — you want that tart brightness.
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