- 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
- Season steak with 1 tsp. salt and 1 tsp. pepper. Let sit at room temperature at least 1 hour.
- 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.
- 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.
- Cut avocados in half crosswise around pit, then carefully peel off skin with your hands. Slice each half crosswise into 1/2″ rings.
- Arrange sliced steak and avocado on platter with pineapple. Drizzle with pineapple dressing; season with salt and pepper.