Preheat the oven to 350F (180C). Lightly grease a loaf pan.
In the bowl of a stand mixer fitted with the paddle attachment, beat the sugar and butter for 2 minutes. Add the eggs and vanilla extract and mix until well incorporated.
In a separate bowl mix the flour with cocoa powder, cinnamon, and baking powder.
Add the rum and red wine to the sugar-egg mixture. Then add the flour mixture. Don’t overbeat the batter, only mix until everything is well incorporated.
Add the chocolate chips and pour the batter into the loaf pan. Bake for 45-50 minutes, a skewer should come out clean with only a few crumbs or melted chocolate attached.
Let the cake sit in the loaf pan for 15 minutes then transfer to a cooling rack and let completely cool off.
Sprinkle powdered sugar over the cake or glaze with chocolate.