Name: Balsamic Grilled Flank Steak with Charred Tomatoes
Prep time: 5 min
Total time: 8 h 20 min
Yield: 6 - 8 serving(s)
Ingredients: 2/3 c. olive oil; 1/2 c. balsamic vinegar; 4 cloves garlic, finely chopped; Kosher salt; Freshly cracked black pepper; 5 to 6 sprigs thyme; 1 (3-pound) piece flank steak (or skirt steak); 1 tbsp. olive oil; 1 shallot, thinly sliced; 3 cloves garlic, sliced; 1 pt. heirloom cherry tomatoes; Kosher salt; Freshly cracked black pepper; 1 shallot, roughly chopped; 2 c. tightly packed fresh basil leaves; 1 clove garlic, peeled; 1/2 tsp. red pepper flakes; 1/2 c. olive oil; 2 tbsp. red wine vinegar; 1 tsp. kosher salt, or to taste; Freshly cracked black pepper

Step 1Make the marinade: In a large nonreactive bowl, whisk together the oil, vinegar, and garlic and season with salt and pepper. Add the thyme. Add the meat to the bowl and flip it to coat. Cover with plastic wrap and refrigerate for at least 8 hours and up to 24 hours.

Step 2Make the charred tomatoes: Heat the oil in your heaviest cast-iron skillet over medium-high heat. Add the shallot and garlic and cook for 1 minute, or until fragrant. Add the cherry tomatoes and cook without stirring for 2 minutes, or until they start to blister. Give them a quick stir, turn off the heat, and let them sit for another 2 minutes or so. Season with salt and pepper.

Step 3Make the basil vinaigrette: In a high-powered blender, combine the shallot, basil, garlic, red pepper flakes, oil, vinegar, and salt and blend for 1 to 2 minutes, until very smooth. Add the salt and season with pepper. The dressing will keep in an airtight container in the fridge for up to 3 days.

Step 4Preheat an outdoor grill or grill pan to medium-high heat and oil the grates. Remove the steak from the marinade, letting excess drip off. Season liberally with salt and pepper. Grill the steak, turning occasionally, until lightly charred all over, 10 to 12 minutes for medium. Transfer the steak to a cutting board and let rest for 5 to 10 minutes.

Step 5To serve, thinly slice the meat against the grain and serve with basil vinaigrette and charred tomatoes on top.