Grate the sharp cheddar if not pre-grated and let the cream cheese sit at room temperature for at least 20 minutes so it softens. This ensures a smooth, spreadable pimento cheese.

In a medium mixing bowl, beat the softened cream cheese with a rubber spatula or electric mixer on low until smooth. Add the mayonnaise and mix until combined and slightly fluffy.

Fold in the grated cheddar and chopped pimentos until evenly distributed. Avoid overmixing; you want a slightly chunky texture.

Season the mixture with powdered sugar, smoked paprika, Worcestershire sauce, lemon juice, kosher salt, black pepper, and cayenne (if using). Taste and adjust seasoning — add more salt or lemon if it needs brightness.

Transfer the pimento cheese to a bowl or directly into serving jars, smoothing the top. Cover and refrigerate while you make the bacon jam, at least 15 minutes to let flavors meld.

Bacon Jam

In a large skillet over medium heat, add the diced bacon. Cook, stirring occasionally, until the fat renders and the bacon is crisp and golden brown, about 8–10 minutes.

Using a slotted spoon, remove 2 tablespoons of the bacon pieces to a small bowl and set aside for garnish. Leave the rendered bacon fat in the skillet (about 1–2 tablespoons). Drain excess fat if there's more than 3 tablespoons, leaving about 2 tbsp in the pan.

Add the finely chopped onion to the skillet and cook in the bacon fat over medium-low heat, stirring frequently, until the onion is soft and caramelized, about 10–12 minutes. If the pan gets dry, add 1–2 tablespoons of water to deglaze and prevent burning.

Stir in the minced garlic and cook for 30–45 seconds until fragrant.

Add the brown sugar, apple cider vinegar, maple syrup, Worcestershire sauce, water, chili flakes, and freshly ground black pepper. Stir to combine, scraping up any browned bits. Simmer gently for 6–8 minutes, until the mixture is thick and jammy.

Return most of the cooked bacon pieces to the skillet (reserve a spoonful for topping). Stir and cook 1–2 more minutes to let the flavors meld and the liquid reduce further. Taste and adjust sweetness, acid, or heat as desired.

Remove from heat and let the bacon jam cool slightly. For a smoother texture, pulse the mixture 2–3 times in a food processor or use an immersion blender briefly — do not purée completely; you want some chunks. Cool to room temperature before assembling with the pimento cheese.

Assembly & Serving

Spoon a generous layer (about 1/2–3/4 cup) of pimento cheese into the bottom of each clean jar until the jar is about one-third full, smoothing the surface.

Spoon a layer of bacon jam (about 1/4–1/3 cup) over the pimento cheese, creating a visible contrast of orange and dark jam. If using larger jars, repeat with another thin layer of pimento cheese and top with more bacon jam for a strata effect.

Finish with the reserved crispy bacon pieces and a sprinkle of sliced chives on top for color and texture. Close jars or cover and refrigerate if not serving immediately.

Serve chilled or at cool-room temperature with crackers or toasted baguette slices. Provide small spoons or spreaders so guests can layer spreads onto crackers. Keeps refrigerated in an airtight container for up to 4–5 days; stir before serving if separated.