- I prefer to use piquillo peppers because they are sharper, sweeter, and more flavorful than canned or jarred pimento peppers, but if you prefer pimentos, substitute them here.
- For best results, use a sturdy loaf of bread, such as Pullman, and slice 3/4-inch thick.
- Pimento cheese yields 2 cups, should you want to serve it on its own.
- For the Pickles
- 4 Kirby (pickling) cucumbers, sliced crosswise into 1/4-inch thick slices
- 1 tablespoon kosher salt
- 1 cup fresh dill, chopped
- 1 tablespoon black peppercorns
- 1 tablespoon dill seeds
- 1 tablespoon mustard seeds
- 1 1/2 cups distilled white vinegar
- 2 tablespoons sugar
- 4 garlic cloves, peeled and smashed
- 1/2 cup ice cubes
- For the Pimento Cheese
- 4 tablespoons mayonnaise
- 1 tablespoon finely grated yellow or white onion
- 2 teaspoons dry mustard
- 1/8 teaspoon cayenne pepper
- 2 cups (8 ounces) extra-sharp orange cheddar cheese, finely grated
- 4 ounces cream cheese, softened
- 2/3 cup drained jarred or canned piquillo peppers, finely chopped (See Notes)
- 1 tablespoon Worcestershire sauce
- Salt and pepper
- Hot sauce (optional)
- For the Assembly
- 8 slices sturdy white sandwich bread (See Notes)
- 6 tablespoons unsalted butter, melted
- 12 slices deli ham
For the Pickles: Toss cucumbers with salt in colander set over bowl. Allow to stand at room temperature for 1 hour. Discard all liquid released by cucumbers.
Place 1/2 cup fresh dill, peppercorns, dill seeds, and mustard seeds in square of cheesecloth and tie together. Place spice bag in medium saucepan along with vinegar, sugar, and garlic and bring to boil over medium-high heat. Add cucumbers and reduce heat to medium-low.
Cook until cucumbers turn dark green, about 5 minutes. Transfer cucumbers and cooking liquid to bowl, add ice, and stir until melted. Chill, uncovered, at least 1 hour before serving. Discard spice bag and garlic and stir in remaining 1/2 cup fresh dill.
Pickles may be made up to 2 weeks ahead and stored, refrigerated, in a covered container.
For the Pimento Cheese: Melt 2 tablespoons mayonnaise in small skillet over medium heat. Add onion, dry mustard, and cayenne and cook, stirring often, until onion is softened, about 3 minutes. Transfer to large bowl and cool to room temperature, about 5 minutes.
Add cheddar cheese, cream cheese, peppers, Worcestershire, and remaining 2 tablespoons mayonnaise to bowl and stir to thoroughly combine. Season to taste with salt, pepper, and (optional) hot sauce.
Pimento cheese may be made up to 1 week ahead and stored, refrigerated, in a covered container. Bring the spread to room temperature prior to using in this recipe or serving.
For the Assembly: Brush one side of each slice of bread with melted butter, then flip so that un-buttered side is facing up.
Spread 1/4 cup pimento cheese on each slice of bread. Arrange 3 slices ham on 4 slices bread. Top ham with enough pickles to cover. Press remaining cheese-spread slices (cheese side down) over pickles.
Heat large skillet or griddle over medium heat. Cook sandwiches until golden and beginning to ooze cheese, 2 to 3 minutes per side. Transfer sandwiches to cooling rack and allow to rest 2 minutes before cutting in half.
Serve with additional pickles.