Cheesy Pineapple Flank Steak Pinwheels

It’s been the most dreary spring here with just a few spots of occasional sun, but when that sun comes it's a rush to take advantage of it. I actually grilled a version of this recipe in the rain that was a complete failure, but I returned to the grill a few days later with renewed confidence and the sun at my back. I have done a lot of pineapple and jalapeno recipes on the site over the years and that play of sweet and spicy is always a winning combo. The main trick to these is rolling them super tight and grilling to a perfect medium to prevent too much of the cheese filling from dripping out.
Cheddar, arugula, jalapenos, and a little cream cheese to help it stick. Slice your flank steak in half the thin way, keeping a little bit intact like a hinge. The hinge should go along the grain. Cheese mixture goes down. Then thin slices of pineapple. Roll it up tight. Put a million skewers in and slice it into pinwheels. Grill on a very high heat for about 6 minutes per side, browning it up nice and cooking the center to medium. The high heat will also help sear the cheese to prevent more from falling out. There is no doubt that there will be cheese leakage here, but we are trying to minimize it. Oh yeaaaaaaa. Allow to rest for 5 minutes before serving to let the cheese congeal a bit. These were so good. The meat was perfectly tender with just enough chew and meaty flavor you expect from flank steak. The spicy and sweet were balanced and the arugula added a nice earthy flavor. And the cheese formed a perfect sauce to complement the steak. Lets hope this dreary weather is done and we can all grill these this weekend!
I served these guys on a simple salad and it was an amazing meal!

Cheesy Pineapple Flank Steak Pinwheels

  • 1.5 pound Flank Steak (bigger is fine)
  • 2 cups Cheddar Cheese
  • 2 tablespoons Cream Cheese
  • 2 Jalapenos diced and most of the seeds removed
  • 2 handfuls Arugula chopped small
  • 1/2 a pineapple cut into thin planks

Instructions

  1. butterfly the flank steak. Cut it the thin way to open it up like a book leaving a hinge along the grain on one side.
  2. mix the cheeses with the jalapeno and arugula until combined.
  3. spread the cheeses on the laid out flank steak. Spread it thin and discard any extra.
  4. Top with a layer of the thin pineapple.
  5. roll up very tight. The grain of the steak should be going along the roll in a straight line, not rolled up with the roll.
  6. Place 3 skewers where each roll will be, and cut in between the skewers to form the pinwheels. Chill to firm for a half hour.
  7. Grill on high heat for about 6 minutes per side to brown and cook to a medium doneness.