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Special equipment: a 4-quart trifle bowl or a 4-quart glass bowl
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For the trifle: Combine the chocolate and butter in a medium bowl.
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Put the bowl over a barely simmering saucepan of water and stir occasionally until the chocolate has melted and the mixture is smooth, about 5 minutes.
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Set aside.
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In another medium bowl, using a fork, gently mash the chestnut puree into 1/2-inch chunks.
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In a stand mixer, fitted with a whisk attachment, beat the cream until thick.
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With the machine running, gradually add the sugar and continue to beat until the cream holds stiff peaks.
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Add half of the whipped cream to the chestnut puree and, using a spatula, fold it in until incorporated.
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Set aside.
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Stir the orange zest and 1/3 of the remaining whipped cream into the chocolate mixture until smooth, then fold in the remaining whipped cream.
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Set aside.
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To assemble the trifle: In the bottom of a 4-quart trifle bowl, arrange a single layer of pound cake slices, trimming the cake slices, if necessary, to fit.
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Drizzle the pound cake with about 1/4 cup of the orange liqueur or orange syrup.
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Spread 1/2 of the chestnut cream on top.
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Arrange another layer of pound cake slices on top and drizzle with 1/4 cup orange liqueur.
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Spread 1/2 of the chocolate cream on top.
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Repeat the layers using the remaining cream and liqueur, finishing with a chocolate cream layer.
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For the garnish: Using a vegetable peeler, shave the chocolate bar on top of the trifle and sprinkle with orange zest.
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Cover the trifle with plastic wrap and refrigerate for at least 3 hours or overnight.
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Allow the trifle to stand at room temperature for at least 1 hour before serving.
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Cook's Note: Chestnut puree can also be made by draining 1 (14-ounce) can of whole chestnuts in water and placing in the bowl of a food processor.
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Add 1/4 cup sugar, 1/8 teaspoon fine sea salt, and 2 tablespoons water.
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Blend until smooth, adding more water, 1 tablespoon at a time until the mixture is a spreadable consistency.
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In a small saucepan, bring the orange juice and sugar to a boil over medium-high heat.
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Simmer, stirring occasionally, until the sugar has dissolved, about 5 minutes.
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Cool for 20 minutes.
