Easter Ham with Golden Breadcrumbs and Madeira Sauce
['1 16-pound whole bone-in smoked ham', '2 cups (packed) dark brown sugar', '1/2 cup Dijon mustard', '1/4 cup extra-virgin olive oil', '3 cups coarse fresh breadcrumbs made from six 1/2"-thick slices rustic white bread', '3 cups Madeira', 'Cheesecloth']
Arrange a rack on lowest level of oven; preheat to 300°F. Without trimming fat, remove outer rind from most of ham, leaving a band around end of shank bone. Spacing cuts 3/4" apart to make a diamond pattern, score fat on top of ham crosswise and then lengthwise on a diagonal (do not cut into meat). Place ham in a large roasting pan. Pour 3 cups water into pan and roast ham for 2 hours.
Meanwhile, stir brown sugar and mustard in a medium bowl until a thick paste forms; set aside. Heat oil in a large skillet over medium heat. Add breadcrumbs; toast, stirring often, until very crispy, 5-7 minutes. Set aside.
Remove ham from oven; increase temperature to 350°F. Spread half of sugar-mustard paste over scored top of ham. Bake until an instant-read thermometer inserted into thickest part of ham registers 145°F, about 1 hour. If pan juices have dried out, add 1 cup water to pan.
Remove ham from oven; increase temperature to 400°F. Spread remaining sugar-mustard paste over ham and pack breadcrumbs all over top.
Bake ham until crumbs are deep golden brown and crisp, 12-15 minutes. Transfer ham to a serving platter; let rest for 20 minutes before carving.
Line a fine-mesh sieve with cheesecloth. Set sieve over a medium pitcher or gravy boat. Spoon off fat from surface of juices in pan; discard. Add Madeira to pan. Place roasting pan over medium-high heat and simmer liquids briskly, scraping up browned bits, until sauce thickens and is reduced to 2 cups, about 15 minutes. Strain sauce through prepared sieve, pressing on solids; discard solids.
Carve ham. Serve sauce alongside.
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