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1
Soak the raisins in the rum overnight and drain just before using.
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2
Butter a 2-quart casserole or gratin dish and preheat the oven to 350F.
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3
Peel the pineapple and remove the eyes.
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4
Slice lengthwise into quarters and cut away the core.
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5
Thinly slice two of the quarters and reserve to use on top of the pudding.
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6
Cut the other two quarters into 1/4-inch cubes.
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7
Combine the wine, 1 cup of the sugar, the pepper flakes, 2 of the cinnamon sticks, the cardamom seeds, cloves, and 1 of the vanilla beans in a small saucepan.
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8
Bring to a boil over high heat, stirring until the sugar has dissolved.
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9
Reduce the heat to medium-low, add the cubed pineapple, and simmer for 10 minutes.
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10
Drain and reserve the syrup and the pineapple cubes.
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11
(Remove and discard the spices from the pineapple.)
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12
Return the syrup to the pan and simmer over medium-low heat until thick, about 5 minutes.
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13
Melt the butter in a large skillet.
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14
Add the bread cubes and cook over medium-high heat, stirring often, until lightly browned, about 5 minutes.
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15
Cool slightly.
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16
Combine the milk, cream, and remaining 1/2 cup sugar in a small saucepan.
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17
Add the remaining cinnamon stick and vanilla bean.
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18
Bring almost to a simmer over medium heat.
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19
Remove from heat and let steep for 5 minutes.
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20
Discard the cinnamon stick and vanilla bean.
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21
Beat the eggs and yolks together in a large heatproof bowl.
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22
Pour the milk and cream mixture into the eggs, stirring constantly.
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23
(Discard the cinnamon stick and vanilla bean.)
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24
Gently stir in the bread cubes and set aside until the bread has absorbed some of the liquid, about 10 minutes.
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25
Mix in the raisins and pineapple cubes, stir well, and pour into the casserole.
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26
Arrange the sliced pineapple decoratively over the top of the pudding, overlapping.
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27
Brush with a small amount of the syrup.
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28
Bake until the pudding is set in the center and lightly browned on top, about 45 minutes.
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29
Serve warm with any remaining syrup on the side.