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1
Tear the bread into bite size pieces and set it out on a cookie sheet to dry. You can either let it sit out all day or pop it in the oven at 200 for 15-20 minutes for a quick-dry.
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2
in a VERY large bowl - whisk together the eggs, sugar, vanilla, cinnamon and nutmeg. Grate a LOT of nutmeg in there - I don't really measure as I grate but maybe 1/3 of a nut's worth. When it is well mixed, whisk in the milk.
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3
Stir in the bread, and really toss it with the milk. You want the bread to soak up all of that wet stuff ... it's a good idea to let it sit for a half hour or so.
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4
While the bread is soaking - cut up the pineapple. You need 2 cups in 1/2 inch chunks. Save the rest for snacks. Put the 2 cups of pineapple in a mixing bowl.
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5
Make the caramel - bring butter, brown sugar, salt and corn syrup to a simmer. Simmer for 5 minutes and then turn off the heat. Pour half the caramel over the pineapple and stir to coat. Bring the other half back to low heat, stir in the cream and rum, and then turn the heat back off.
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6
Check your bread and give it a stir. Heat the oven to 350.
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7
Butter a 9x13 (3 quart) pyrex - or another prettier 3 qt baking dish if you have one. If the bread is ready and nice and juicy ... spread half into the pyrex. Spread the pineapple mixture evenly across the bread and then top with the remaining bread - if there is any eggy milky liquid in the bowl pour that in too. At this point if any bread pieces are crust side up I flip them over so the crust won't get too hard during baking.
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8
Bake at 350 until the pudding is set - this will depend on your pan - mine took about an hour and 20 minutes. You want some good crunchies on top but no burned stuff.
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9
Warm you rum caramel up a bit - scoop the pudding into bowl and drizzle a little of that goodness over, and enjoy!
