In a small saucepan over medium heat, combine the finely chopped pineapple, light brown sugar, granulated sugar, grated ginger, red pepper flakes, and 1/8 tsp salt. Stir and bring to a gentle simmer.

Reduce heat to medium-low and cook, stirring occasionally, until the pineapple breaks down and the mixture thickens, about 12–15 minutes. Mash larger pieces with the back of a spoon for a jam-like texture.

Remove from heat and stir in the bourbon, lime juice, and apple cider vinegar. Taste and adjust sweetness or acidity as needed. Let cool to room temperature; jam will thicken further as it cools.

Thai Pickled Onions

Quick-pickle onions

Place thinly sliced red onion and optional sliced thai bird chiles in a heatproof jar or bowl.

In a small saucepan, combine rice vinegar, water, sugar, 1/2 tsp salt, fish sauce, and lime zest. Warm just until the sugar dissolves (do not boil).

Pour the warm brine over the onions, pressing to ensure they are submerged. Let cool to room temperature, then cover and refrigerate at least 30 minutes (ideally 1 hour) before using. Keeps up to 2 weeks refrigerated.

Sandwich

Prepare beef

Pat the beef tenderloin dry with paper towels. Season all over with 1 tsp salt and 1/2 tsp black pepper. Let rest at room temperature for 15 minutes while pickles and jam are finishing.

Heat a heavy skillet or cast-iron pan over medium-high heat until very hot. Add 1 tbsp olive oil and swirl to coat. Sear the tenderloin on all sides until a brown crust forms, about 1–2 minutes per side.

Reduce heat to medium and continue cooking, turning occasionally, until an instant-read thermometer inserted into the center reads 125°F (52°C) for medium-rare, about 6–10 minutes depending on thickness. For medium, cook to 135°F (57°C).

Transfer the beef to a cutting board and let rest tented loosely with foil for 8–10 minutes to allow juices to redistribute.

Toast rolls & assemble

While beef rests, split the ciabatta rolls and lightly butter the cut sides. Toast them in a hot skillet or under a broiler until golden, about 1–2 minutes.

Slice the rested tenderloin thinly against the grain into 1/4-inch slices.

To assemble each sandwich: spread about 1 to 1.5 tablespoons of bourbon pineapple jam on the bottom half of each roll. Layer 3–4 slices of tenderloin (about 3 oz per sandwich), then scatter about 2 tablespoons of thai pickled onions over the beef. Top with a small handful (about 1/2 cup) of arugula and sprinkle 2 tablespoons of crumbled bleu cheese. Close with the top roll.

If desired, press the sandwich lightly and serve immediately while warm.