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Grilled Chicken and Kale Caesar Pressed Sandwich

In this satisfying, do-ahead sandwich, the kale salad gets more flavorful and tender as it sits. It's perfect for a picnic!
Cook Time 25 minutes
Total Time 5 hours 5 minutes
Course lunch/dinner
Cuisine American
Servings 8 people
Calories 2888.3 kcal

Equipment

  • 1 Grill Pan
  • 1 Baking Sheet Lined with parchment paper
  • 2 Mixing Bowls One small for dressing, one large for kale
  • 1 Instant-Read Thermometer For ensuring chicken is cooked through
  • 1 Cast-Iron Skillet or Heavy Object For pressing the sandwich

Ingredients
  

Main

  • 2 boneless skinless chicken breasts about 1 pound total
  • Kosher salt and freshly ground black pepper
  • 2 tablespoons extra-virgin olive oil plus more for drizzling
  • 6 slices thick-cut bacon about 8 ounces
  • 8- inch round sourdough loaf
  • 1/2 cup mayonnaise
  • 1/4 cup grated Parmesan
  • 2 anchovies packed in oil finely minced
  • 1 small clove garlic grated
  • Zest and juice of 1 lemon
  • 8 ounces kale washed, stems removed and leaves thinly sliced
  • 5 radishes thinly sliced
  • 1/2 English cucumber thinly sliced on the bias

Instructions
 

  • Preheat a grill pan over medium-high heat. Put the chicken breasts in a medium bowl. Sprinkle with 3/4 teaspoon salt, a few grinds of pepper, and a drizzle of olive oil; toss to coat. Let sit at room temperature for 15 minutes.
  • Meanwhile, preheat the oven to 375 degrees F. Line a baking sheet with parchment and arrange the bacon strips on top. Bake, flipping once halfway through, until the bacon is golden brown and crisp, about 25 minutes. Transfer to a paper-towel lined plate.
  • Grill the chicken until an instant-read thermometer inserted in the middle of the chicken reads 165 degrees F, 6 to 8 minutes per side. Let cool, then slice thinly across the grain.
  • Slice the sourdough loaf in half horizontally and lay the two halves cut-side up. Scoop out some of the bread from both halves and reserve for another use.
  • Whisk the mayonnaise, Parmesan, anchovies, garlic, lemon zest and juice, 1/4 teaspoon salt, a few grinds of black pepper and the remaining 2 tablespoons olive oil together in a small bowl. Remove 1/4 cup of the dressing and add it to a large bowl along with the kale. Toss to coat and season to taste with more salt and pepper.
  • Spread the remaining salad dressing on both halves of the bread. Building on the bottom half, layer half the kale salad, bacon, sliced chicken, and a sprinkle of salt. Place the radishes on top of the chicken in a single layer, then add the cucumber in a single layer. Scoop the remaining kale salad into the top half of the bread, and place on top of the sandwich. Wrap tightly in parchment, wax paper or plastic wrap and secure with twine if necessary. Place a brick (see Cook's Note) or cast-iron skillet on top for at least 3 hours to flatten, refrigerated. About 45 minutes before serving, bring the sandwich to room temperature.

Notes

The pressing step is paramount for this sandwich; it allows flavors to meld beautifully and compresses the ingredients, preventing sogginess and making for a cohesive bite. Ensure your pressing weight (like a cast-iron skillet or culinary bricks) is substantial for best results. Pre-salting the chicken before grilling enhances its flavor and juiciness. For the kale, thinly slicing and tossing with dressing ahead of time tenderizes it significantly, making it less fibrous and more palatable. Don't skip scooping out the sourdough crumb; this creates space for ample filling without making the sandwich unwieldy.