Smoky Grilled Pineapple Mezcal Old-Fashioned with Brown Butter-Pineapple Syrup

How to Make Smoky Grilled Pineapple Mezcal Old-Fashioned with Brown Butter-Pineapple Syrup

1. 1

   Step 1: Prep grill, cut pineapple for syrup and garnish

   Preheat the grill to medium-high (about 400–450°F / 205–230°C). Trim and core the pineapple: cut four 1/2–3/4-inch wheels (reserve for garnish) and cut the remaining flesh into 2–3 cm chunks for the syrup. Place the chunks in a bowl and set the pineapple wheels on a plate to be charred later.

   For this step

   • 1 small pineappleFresh ripe pineapple
   
2. 2

   Step 2: Brown butter and caramelize pineapple on a cast-iron griddle or grill

   Set a cast-iron griddle on the grill (or use a cast-iron skillet directly on the grate) and melt the unsalted butter over medium heat. Swirl continuously until the butter foams and takes on a nutty-brown color and aroma (2–4 minutes) — watch closely to avoid burning. Add the pineapple chunks to the griddle and sear until deeply caramelized and slightly charred (3–5 minutes per side); scrape browned bits into the butter. Sprinkle the dark brown sugar over the pineapple and pour in the water, stirring to dissolve sugar and deglaze the griddle, then simmer gently until the mixture thickens to a syrupy consistency (about 6–10 minutes).

   For this step

   • 4 tbspUnsalted butter
   • 1 cupDark brown sugar (packed)
   • 1/2 cupWater
   
3. 3

   Step 3: Finish, strain, and cool the brown butter–pineapple syrup

   Carefully remove the griddle from the heat. For a smooth syrup, press the mixture through a fine-mesh strainer into a heatproof container, pressing on solids to extract as much liquid as possible; discard solids or reserve a few caramelized chunks for garnish. You should yield roughly 1 cup (240 ml) of syrup — enough for ~4 cocktails at 1/2 oz (15 ml) each plus extra for glazing. Let the syrup cool to room temperature (15–20 minutes) and chill if not using immediately.
   
4. 4

   Step 4: Cocktail ratios and build (per cocktail)

   Per cocktail: 2 oz (60 ml) mezcal, 1/2 oz (15 ml) brown-butter pineapple syrup, and 2 dashes smoked bitters. Add ingredients to a mixing glass with plenty of ice and stir 20–30 seconds until well chilled and slightly diluted. Strain over a single large ice cube in an Old-Fashioned glass. If desired, moisten the rim with a little syrup and dip in smoked sea salt for a savory edge.

   For this step

   • 8 fl ozMezcal
   • 8 dashSmoked bitters (Angostura or similar)
   • 8 cubeLarge ice cubes / single large cubes
   • 1/4 tspSmoked sea salt (optional, for rim)
   • 4 stripFresh orange peel (expressed, 1 strip per cocktail)
   
5. 5

   Step 5: Charred-pineapple wheel garnish and smoke-level options

   While cocktails are being mixed, place the reserved pineapple wheels directly on the hot grill and char 1–2 minutes per side until deeply browned and smoky — slide under a hotter spot briefly for extra char. Garnish each glass with a charred pineapple wheel and express an orange peel over the top, rubbing the rim. To control smoke level: for lighter smoke, char briefly and avoid extra wood; for medium smoke, use 10–15 minutes of indirect wood-chip smoke (apple or cherry) before searing; for high smoke, use mesquite or hickory chips, leave pineapple over direct heat longer, or choose a peaty/peat-influenced mezcal. A smoked salt rim and extra toasted char will intensify the campfire note.
   
6. 6

   Step 6: Backyard entertaining timeline and grill pairings

   Timeline: start 45 minutes before serving — 10 minutes to preheat grill and prep pineapple, 20–25 minutes to brown butter, caramelize and reduce into syrup, 15 minutes to cool; cocktails are quick to build to order (2–3 minutes each). Pairings: steak — high-heat grilled ribeye or skirt steak (reverse-sear or hot-and-fast) seasoned with coarse salt, cracked pepper, and a finishing herb butter or chimichurri; cook ribeye to 125–130°F (rare–medium-rare) and rest. Pork — bone-in pork chops or a pork shoulder steak brushed with a little of the pineapple syrup and finished on the grate; season with salt, smoked paprika, and garlic, cook to 145°F and rest. Both proteins benefit from a brief finishing char to echo the cocktail’s grilled-smoke profile.
   

1. Preheat the grill to medium-high (about 400–450°F / 205–230°C). Trim and core the pineapple: cut four 1/2–3/4-inch wheels (reserve for garnish) and cut the remaining flesh into 2–3 cm chunks for the syrup. Place the chunks in a bowl and set the pineapple wheels on a plate to be charred later.
2. Set a cast-iron griddle on the grill (or use a cast-iron skillet directly on the grate) and melt the unsalted butter over medium heat. Swirl continuously until the butter foams and takes on a nutty-brown color and aroma (2–4 minutes) — watch closely to avoid burning. Add the pineapple chunks to the griddle and sear until deeply caramelized and slightly charred (3–5 minutes per side); scrape browned bits into the butter. Sprinkle the dark brown sugar over the pineapple and pour in the water, stirring to dissolve sugar and deglaze the griddle, then simmer gently until the mixture thickens to a syrupy consistency (about 6–10 minutes).
3. Carefully remove the griddle from the heat. For a smooth syrup, press the mixture through a fine-mesh strainer into a heatproof container, pressing on solids to extract as much liquid as possible; discard solids or reserve a few caramelized chunks for garnish. You should yield roughly 1 cup (240 ml) of syrup — enough for ~4 cocktails at 1/2 oz (15 ml) each plus extra for glazing. Let the syrup cool to room temperature (15–20 minutes) and chill if not using immediately.
4. Per cocktail: 2 oz (60 ml) mezcal, 1/2 oz (15 ml) brown-butter pineapple syrup, and 2 dashes smoked bitters. Add ingredients to a mixing glass with plenty of ice and stir 20–30 seconds until well chilled and slightly diluted. Strain over a single large ice cube in an Old-Fashioned glass. If desired, moisten the rim with a little syrup and dip in smoked sea salt for a savory edge.
5. While cocktails are being mixed, place the reserved pineapple wheels directly on the hot grill and char 1–2 minutes per side until deeply browned and smoky — slide under a hotter spot briefly for extra char. Garnish each glass with a charred pineapple wheel and express an orange peel over the top, rubbing the rim. To control smoke level: for lighter smoke, char briefly and avoid extra wood; for medium smoke, use 10–15 minutes of indirect wood-chip smoke (apple or cherry) before searing; for high smoke, use mesquite or hickory chips, leave pineapple over direct heat longer, or choose a peaty/peat-influenced mezcal. A smoked salt rim and extra toasted char will intensify the campfire note.
6. Timeline: start 45 minutes before serving — 10 minutes to preheat grill and prep pineapple, 20–25 minutes to brown butter, caramelize and reduce into syrup, 15 minutes to cool; cocktails are quick to build to order (2–3 minutes each). Pairings: steak — high-heat grilled ribeye or skirt steak (reverse-sear or hot-and-fast) seasoned with coarse salt, cracked pepper, and a finishing herb butter or chimichurri; cook ribeye to 125–130°F (rare–medium-rare) and rest. Pork — bone-in pork chops or a pork shoulder steak brushed with a little of the pineapple syrup and finished on the grate; season with salt, smoked paprika, and garlic, cook to 145°F and rest. Both proteins benefit from a brief finishing char to echo the cocktail’s grilled-smoke profile.