How to Make It
Prepare the Eggnog Pudding: Combine sugar, cornstarch, and salt in a large saucepan. Whisk in yolks; slowly drizzle in milk until smooth, whisking constantly. Cook over medium-high, whisking occasionally, until mixture begins to boil, 6 to 7 minutes. Cook until thickened, whisking constantly, 5 to 7 minutes. Stir in butter, bourbon, if desired, and nutmeg. Spoon custard into a large bowl (you will need space to fold in whipped cream later); cover with plastic wrap, pressing it directly on surface of pudding, and chill until cooled, 2 to 3 hours.
Prepare the Brandied Cherries: Place all Brandied Cherries ingredients in a saucepan over medium-high. Bring to a boil, stirring often, 6 to 7 minutes. Reduce heat to medium, and cook until juices have thickened, 10 to 12 minutes. Remove from heat; cool to room temperature.
Prepare the Candied Bacon: Preheat oven to 425°F. Arrange bacon in a single layer on a rack set over a rimmed baking sheet. Bake in preheated oven until cooked through and crispy, about 20 minutes. Reduce oven temperature to 325°F. Brush bacon with jelly, and cook about 12 minutes, checking it after 8 to 10 minutes. (Be careful, it can burn easily!) Remove from oven; cool to room temperature.
When pudding has chilled, remove plastic wrap, and whisk pudding vigorously until smooth. Gently fold in 2 cups of the whipped cream.
Assemble the trifle: Arrange half of the pound cake cubes in the bottom of an 8-cup trifle dish. Top with half of the Eggnog Pudding mixture, half of the cookies, and half of the Brandied Cherries. Repeat layers, reserving 6 to 8 cherries. Top final cherry layer with remaining 2 cups whipped cream. Chill trifle 2 to 4 hours to let flavors meld. Break Candied Bacon into shards. Arrange Candied Bacon and reserved Brandied Cherries on top of whipped cream.