Chimichurri Stuffed Grilled Flank Steak

Tender flank steak is filled with a bold, garlicky chimichurri made with fresh parsley, oregano, red wine vinegar, and olive oil, then tightly rolled and grilled until beautifully charred outside and juicy inside. Sliced into colorful steak pinwheels and finished with fresh chimichurri, it's a flavorful, impressive meal that's surprisingly lean and simple to prepare.

Great

% Daily Values based on a 2,000 calorie diet

Step 1

Combine the parsley, garlic, oregano, vinegar, olive oil, salt, pepper and red pepper flakes.

Step 2

Unlike a traditional chimichurri, this should be fairly thick and paste-like. We're deliberately limiting the oil and vinegar so it stays inside the steak instead of pouring out onto the grill.

Step 3

Taste it. You want it intensely garlicky, herby and acidic because it's seasoning a substantial amount of beef.

Step 4

Prepare the steak

Step 5

Lay the flank steak on a cutting board with the grain running left-to-right.

Step 6

If it's particularly thick, carefully butterfly it horizontally so you can open it like a book. Otherwise, cover it with plastic wrap and gently pound the thicker areas until the steak is an even ½–¾ inch thick.

Step 7

Season the inside lightly with salt and pepper.

Step 8

Spread the thick chimichurri evenly over the steak, leaving roughly a 1-inch border around the edges.

Step 9

If using feta, sprinkle a light layer over the chimichurri. I wouldn't go crazy with it—we want steak and chimichurri, not stuffed cheese steak.

Step 10

Roll it

Step 11

Here's the important part: roll across the grain.

Step 12

You ultimately want to slice the cooked roll so you're cutting across the steak's muscle fibers. That gives you tender pinwheels rather than long, chewy strands.

Step 13

Roll it tightly into a log and tie it with butcher's twine approximately every 1½–2 inches.

Step 14

Lightly coat the outside with olive oil and season with salt and pepper.

Step 15

Grill

Step 16

Set up the grill for two-zone cooking, with a hot direct side and a cooler indirect side.

Step 17

Sear the steak roll over direct heat, rotating it every couple of minutes until you've developed good browning around the entire outside.

Step 18

Then move it to indirect heat, close the lid, and continue cooking until the center reaches approximately 125–130°F for medium-rare or 135°F for medium.

Step 19

Because you've rolled the steak, expect roughly 15–25 minutes of indirect cooking, but thickness matters considerably more than time. A meat thermometer is your friend here.

Step 20

Remove it from the grill and rest for 10 minutes.

Step 21

Serve

Step 22

Remove the twine and slice the roll crosswise into roughly ¾-inch pinwheels.

Step 23

I'd make a little additional traditional chimichurri—looser and heavier on the olive oil and vinegar—to spoon over the finished slices. That's where you'll get that bright, fresh chimichurri hit.

Step 24

For this week's leaner menu, I'd plate it with crispy oven-roasted baby potatoes and grilled asparagus.

Step 25

One other variation occurs to me that could be really good: add a thin layer of roasted red peppers inside with the chimichurri. You'd get green chimichurri, bright red pepper and steak in every pinwheel, while adding sweetness and moisture for very few additional calories.