Pat the beef tenderloin steaks dry with paper towels. Season both sides evenly with kosher salt and freshly ground black pepper. Let sit at room temperature for 20–30 minutes (optional) to take the chill off and promote even cooking.

Cook steaks

Heat a heavy skillet (cast iron preferred) over medium-high heat until very hot. Add 1 tablespoon neutral oil and swirl. Sear steaks 2–3 minutes per side for medium-rare (internal temp ~130°F / 54°C), adding 1 tablespoon butter to the pan in the last 30–60 seconds and spooning it over the steaks. Adjust time for thickness and desired doneness. Transfer steaks to a cutting board and rest 5–7 minutes, then slice thinly against the grain for sandwiches.

Bourbon Pineapple Jam

Combine finely chopped pineapple, light brown sugar, grated ginger, red pepper flakes, lime juice, apple cider vinegar, and kosher salt in a small saucepan. Bring to a gentle simmer over medium heat, stirring occasionally. Cook until the mixture thickens and the pineapple is jammy, about 10–12 minutes. Stir in bourbon and simmer 1–2 minutes more to meld flavors (you may flame briefly if desired and safe). Remove from heat and let cool slightly; mixture will thicken further as it cools. Taste and adjust salt, sugar, or acidity.

Smashed Avocado

Halve and pit the ripe avocado. Scoop the flesh into a bowl and lightly smash with a fork until mostly smooth with some texture. Stir in lemon or lime juice, salt, pepper, and chopped cilantro if using. Adjust seasoning to taste. Keep covered until assembly to prevent browning.

House Sauce

In a small bowl, whisk together mayonnaise, Dijon mustard, Worcestershire sauce, hot sauce, lemon juice, grated garlic, smoked paprika, and black pepper until smooth. Taste and adjust heat, acidity, or salt as needed. Refrigerate until ready to use.

Assembly & Extras

Toast rolls: Spread butter on cut sides of the rolls. Heat a skillet over medium and toast rolls, buttered-side down, until golden and crisp, about 1–2 minutes. Remove from pan.

Build sandwiches: Spread about 1 tablespoon house sauce on both toasted roll bottoms and tops. On the bottom roll, spread 2–3 tablespoons smashed avocado. Top avocado with a layer of thinly sliced resting steak (about 3–4 oz per sandwich), then a generous spoonful (about 1–2 tablespoons) of bourbon pineapple jam, a few dill pickle slices, and a small handful of arugula or baby greens if using. Cap with the top roll. Repeat to assemble remaining sandwiches.

Serve: Cut sandwiches in half if desired and serve immediately so the bread remains crisp. Leftover jam keeps refrigerated up to 1 week; sauce up to 5 days.