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Preheat an outdoor grill for high heat and lightly oil the grate.
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Place the sugar in a mixing bowl. Gradually add the salt, mixing as you go and tasting along the way, until there’s enough salt that the flavor comes through but doesn’t overpower the sugar. With protective gloves or your bare fingers, massage in the chile so the flavor spreads throughout and the mix tastes sweet with a hint of salt and heat. Wash your hands thoroughly (ideally before putting your fingers near your eyes!).
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Slice off the pineapple top along with enough pineapple for the top to stand upright. Set aside.
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Cut off and discard the pineapple’s brown outer skin, then slice the flesh into 1-inch-thick rounds. With a knife, core the tough center of each round, then grill the pineapple rings until grill marks appear, 2 to 3 minutes per side. Let cool, then slice into 2- to 3-inch wedges.
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Stand the pineapple top on a serving platter. Surround it with the grilled pineapple wedges, sprinkle with the spiced-sugar dip, and serve with extra dip.