Sangria-Marinated Skirt Steak with Hearts of Romaine à la Caesar

Sangria-Marinated Skirt Steak:

• 2 cups Rioja wine
• 3 cloves garlic, smashed
• 3 thyme sprigs, leaves picked
• 1 orange, sliced with the peel on
• 1 shallot, sliced
• 1/4 cup olive oil
• 1 pound trimmed skirt steak

Toasted Bread Crumbs:

• 2 teaspoons butter
• 1 tablespoon panko bread crumbs
• 1 clove garlic, chopped
• 1 teaspoon parsley, chopped

Caesar Dressing:

• 1 egg yolks
• 1/2 anchovy fillet
• 2 tablespsoons grated Parmesan 
• Juice of 1/4 lemon
• 1 1/2tablespoons red vinegar
• 1/2 tablespoon Dijon mustard
• 1/2 teaspoon cracked black pepper
• Dash of Worcestershire sauce 
• Dash of Tabasco
• 1/2 cup canola oil

Hearts of Romaine à la Caesar:

• 2 hearts of romaine
• Caesar Dressing
• Salt and pepper to taste

Make the marinade: pour the Rioja wine into a vessel large enough to fit the steak. Add the smashed garlic, thyme sprigs, orange slices, shallots, and olive oil. Place the trimmed skirt steak in the marinade and refrigerate for a minimum of 6 hours.

Make the bread crumbs: in a large sauté pan, melt the butter over medium heat. Add the bread crumbs and toast them until golden and you smell a pleasant nutty aroma, about 1 minute. Add the chopped garlic and toast for 45 seconds. Add the parsley, and immediately remove the bread crumbs from the pan to a towel-lined sheet pan or plate to drain and cool.

Make the dressing: in a food processor, add all of the ingredients except the oil. While the processor is still running, slowly add the oil in a constant, steady stream, being careful not add the oil too quickly, as this will cause the dressing to separate.

Assemble the dish: heat your grill or grill pan over high  heat. Remove the steak from the marinade, season it with salt and pepper on both sides, and grill it for 4 minutes on each side for medium-rare. Remove the steak from the grill and allow it to rest.

Slice the romaine hearts lengthwise into quarters. Brush the leaves with the dressing and grill them until they are slightly wilted and the dressing has browned, about 30 seconds to 1 minute. Slice the skirt steak against the grain and place it on top of the grilled romaine.  Sprinkle the toasted bread crumbs on top and serve.