Pre-heat oven to 350 degrees. Grease and flour three 8-inch cake pans and set aside.
Chop the cherries and place on a few sheets of paper towel to drain and dry.
Whisk together the flour, baking powder, baking soda and salt. Set aside.
Using an electric mixer, beat the butter until smooth. Add the sugar and mix on medium speed until light and fluffy.
With the mixer on medium-low, add in the vanilla and whole eggs – one at a time. Stop the mixer and scrape down the bowl.
In a separate bowl, combine the buttermilk and cherry syrup and set aside.
Working in alternating batches, add half of the dry ingredients to the butter/eggs and mix on low until combined. Stream in the cherry buttermilk and mix until incorporated. Add in the remaining dry ingredients and a drop or two of pink food coloring (if using). Mix until combined. The batter should be fairly thick.
In a clean, dry bowl, whisk the egg whites on high until medium-firm peaks. Meanwhile, toss the chopped cherries in the 2 tablespoons of reserved flour.
Using a spatula, fold the cherries and chocolate chips into the batter. Add in about 1/3 of the whipped egg whites and mix until combined and the batter lightens up slightly. Add the remaining egg whites and gently fold until the batter is smooth.
Evenly distribute the batter between the cake pans and bake for 24 to 26 minutes, or until a toothpick inserted into the center of the cakes comes out clean. Cool on a wire rack for 15 to 20 minutes before removing the cakes from their pans.
For the Bittersweet Ganache:
Place the chocolate in a heat-safe bowl and set aside. Heat the cream in a small saucepan over medium-high heat until it just begins to simmer.
Pour the cream over the chopped chocolate and let sit for 30 to 60 seconds. Whisk until smooth. Allow to cool and thicken before using. You may cool the ganache in the refrigerator, but be sure to stir every so often to remain smooth.
For the Whipped Vanilla Frosting:
Using an electric mixer, beat the butter on medium until smooth.
With the mixer on low, gradually add in the remaining ingredients. Once the sugar begins to incorporate, turn the mixer up to medium-high and mix until light and fluffy (3 to 5 minutes).
Adjust the sugar and milk quantities until desired consistency is achieved. When done, the frosting should be nearly white.
For the Assembly:
Once the cakes are completely cool (or chilled) and ganache has thickened, place one layer of cake onto a serving plate and top with a thin layer of ganache. Place about ¾ cup of frosting on top and smooth with an offset spatula. Top with the next layer of cake, ganache, frosting and final layer of cake. Crumb coat the cake with the frosting and chill for 15 minutes.
Reserve some white frosting for the swags and rosettes, then tint the remaining frosting blue.*
Frost and smooth cake with blue buttercream to your liking.
Use a medium star tip, like a Wilton 1B, to pipe white swags around the sides of the cake. At the top of each swag, pipe a small rosette and plop on a cherry!
* This cake and decoration uses every last bit of frosting in this recipe. To make sure you don’t tint too much of it blue, first practice your swags and piping on the crumb coat. Gently scrape off the decorations and set aside (keep this frosting white!), before tinting the remaining frosting blue to use for the tops/sides of the cake.