Philadelphia Roast Pork Sandwiches

Our take on Philadelphia Roast Pork Sandwiches combines roasted pork with melty provolone cheese and broccoli rabe for a seriously satisfying bite. We sautéed the broccoli rabe with plenty of garlic and some crushed red pepper flakes, and finished it with fresh lemon juice. Its bitterness and brightness balances the fattiness of the pork, which is incredibly tender and buttery with a flavorful crust. Letting the pork sit at room temperature for an hour while the oven preheats helps ensure it cooks evenly. Roasting it initially at 450°F and then lowering the oven temperature crisps and renders the fat on top, and then slowly cooks the meat. The provolone brings sharpness and helps keep the bottom of the roll from getting too soggy, and the mayo — which has a punch of acidity from pickled pepperoncini and its brine — is the finishing touch.

Philadelphia Roast Pork and Broccoli Rabe Sandwiches
Photo: Photo by Fred Hardy / Food Styling by Ali Ramee / Prop Styling by Christina Brockman
Active Time:
40 mins
Total Time:
3 hrs 45 mins


  • 1 tablespoon fennel seeds

  • 1 tablespoon light brown sugar

  • 1 tablespoon finely chopped fresh rosemary

  • 1 ½ teaspoons finely chopped fresh thyme

  • cup, plus 2 tablespoons extra-virgin olive oil, divided

  • 1 ½ tablespoons, plus 1 teaspoon kosher salt, divided

  • 1 teaspoon crushed red pepper, divided

  • 1 (3-pound) boneless pork shoulder (Boston butt), fat cap trimmed to 1/4 inch

  • ¾ cup mayonnaise

  • 3 tablespoons finely chopped pickled pepperoncini plus 1 1/2 tablespoons pickle brine (from 1 [12-ounce] jar)

  • ½ teaspoon grated garlic (from 2 medium garlic cloves)

  • 6 large garlic cloves, thinly sliced (3 tablespoons)

  • 1 pound fresh broccoli rabe, leaves and tender stems chopped (woody ends discarded) (about 8 cups)

  • 1 tablespoon fresh lemon juice (from 1 lemon)

  • 6 hearty seeded round sandwich rolls, split

  • 12 (3/4-ounce) sharp provolone cheese slices


  1. Cook fennel seeds in a small skillet over medium, stirring often, until toasted and fragrant, about 2 minutes. Transfer to a small bowl; let stand until completely cooled, about 5 minutes.

  2. Place cooled fennel seeds in a spice grinder; grind into a powder, about 15 seconds. Return to small bowl; stir in sugar, rosemary, thyme, 2 tablespoons of the oil, 1 1/2 tablespoons of the salt, and 1/2 teaspoon of the crushed red pepper. Rub mixture evenly over pork to completely coat. Place pork on a wire rack set inside a large rimmed baking sheet lined with aluminum foil. Let stand at room temperature for 1 hour. Meanwhile, preheat oven to 450°F.

  3. Roast pork in preheated oven until browned on top, about 20 minutes. Without opening oven, reduce oven temperature to 300°F. Continue roasting until a thermometer inserted into thickest portion of meat registers 165°F, 1 hour, 45 minutes to 2 hours. Remove from oven. Transfer pork to a cutting board set inside a rimmed baking sheet to catch juices. Loosely cover pork with aluminum foil; let rest at room temperature 30 minutes. Slice pork as thinly as possible. Transfer to a medium bowl, along with any carving juices. Add 1/4 teaspoon of the salt, and toss to combine.

  4. While pork rests, stir together mayonnaise, chopped pepperoncini with brine, and grated garlic in a small bowl. Set aside until ready to use.

  5. After about 20 minutes of pork resting time, heat sliced garlic and remaining 1/3 cup oil in a large Dutch oven or a deep, large skillet over medium, stirring often, until garlic turns light golden, about 5 minutes. Add broccoli rabe and remaining 1/2 teaspoon crushed red pepper. Increase heat to medium-high; cook, stirring often, until broccoli rabe stems are tender-crisp, about 4 minutes. Remove from heat; stir in lemon juice and remaining 3/4 teaspoon salt.

  6. Preheat oven to broil with rack about 10 inches from heat. Arrange rolls, cut side up, on a large rimmed baking sheet. Place 2 provolone slices on each bottom roll. Broil in preheated oven until cheese is melted, 1 to 2 minutes. Remove from oven. Divide pork evenly among bottom rolls. Top each with 1/3 cup broccoli rabe mixture. Spread 2 1/2 tablespoons mayonnaise mixture onto each top bun half. Cover sandwiches with top buns. Serve.

Related Articles