Skirt Steak and Broccoli Rabe

Ingredients

•     Medium-bodied red wine, ¾ cup
•     Garlic, 2 small cloves (smashed) plus 8 whole medium cloves
•     Shallot, ½ medium (thinly sliced)
•     Freshly ground black pepper, 1 tablespoon plus extra for seasoning
•     Skirt steak, two 6-ounce pieces (trimmed of extra fat)
•     Extra-virgin olive oil, 1½ cups plus 2 tablespoons, divided
•     Red pepper flakes, ½ teaspoon
•     Broccoli rabe, 1 large bunch (tough stems removed and stalks cut into 3-inch-long pieces)
•     Water, 2 tablespoons
•     Kosher salt
•     Canola oil, 1 tablespoon

Directions

1.     In a gallon-size resealable plastic bag or airtight container, add the: Red wine Smashed garlic Sliced shallot 1 tablespoon ground black pepper Skirt steaks Seal the bag or container and refrigerate for at least 1 hour or up to 3 hours.
2.     Meanwhile, make the garlic confit: In a small saucepan set over low heat, add the: Whole garlic cloves 1½ cups extra-virgin olive oil Cook until the garlic is soft but not browned and a paring knife easily slips into the center of a clove, 20 to 30 minutes. Use the slotted spoon to remove the garlic from the oil (save the oil for another time).
3.     In a large pot or Dutch oven set over medium heat, add: 2 tablespoons extra-virgin olive oil Red pepper flakes Cook until fragrant (take care not to let the red pepper flakes burn), 20 to 30 seconds. Add the: Broccoli rabe Water Season to taste with: Kosher salt Ground black pepper Cover the pot and cook for 1 minute, then add the oil-poached garlic. Use the wooden spoon to quickly stir, cover and continue to cook until the broccoli rabe is tender, 2 to 4 minutes. Remove the lid and cook until the liquid is evaporated, about 4 minutes. Set aside.
4.     Remove the steaks from the marinade and use paper towels to pat dry. Liberally season both sides with: Kosher salt Freshly ground black pepper 5. Set a medium heavy-bottomed skillet over high heat until nearly smoking, 1½ to 2 minutes. Add the: Canola oil Add the seasoned steaks and sear until browned on both sides, about 2 minutes per side for medium-rare. Use tongs to transfer to a cutting board to rest for 5 minutes before slicing into thin strips crosswise and against the grain. Serve with the broccoli rabe.