Ingredients

• 2 pounds New York strip steak (about 3 [1"-thick] steaks)
• 1 1/2 teaspoons kosher salt, divided, plus more
• 1 teaspoon freshly ground black pepper, plus more
• 1 pineapple, peeled, cut into 1/2" rounds, center core removed, divided
• 3 tablespoons olive oil, plus more for grill
• 2 avocados

Instructions

1. Season steak with 1 tsp. salt and 1 tsp. pepper. Let sit at room temperature at least 1 hour.
2. Meanwhile, purée 1 pineapple round, 1/2 tsp. salt, and 2 Tbsp. water in a blender until smooth. Add 3 Tbsp. oil and blend until smooth; set aside.
3. Prepare a grill for medium-high heat or heat a grill pan over medium-high; oil grate or pan. Grill steaks and remaining pineapple rounds, turning occasionally, until pineapple is lightly charred and an instant-read thermometer inserted into the center of steak registers 120°F, 8–10 minutes for medium-rare (pineapple may take longer to cook than steak). Transfer steak to a cutting board. Let sit at least 15 minutes, then thinly slice. Transfer pineapple to a platter and tent with foil to keep warm.
4. Cut avocados in half crosswise around pit, then carefully peel off skin with your hands. Slice each half crosswise into 1/2" rings.
5. Arrange sliced steak and avocado on platter with pineapple. Drizzle with pineapple dressing; season with salt and pepper.