Preheat the oven to 350 degrees Fahrenheit and position the racks toward the center. Line cupcake pans with papers. Combine flour, baking soda, salt and sugar, whisking to blend; set aside.
In a heavy-bottomed, medium pan, melt the butter on medium-high heat. Once melted, add the coffee and whisk together. Add the espresso powder and cocoa--gradually--whisking to combine. The mixture should come to a simmer, but not a boil. You want it to thicken.
Once thickened, cool the cocoa mixture for about 10-15 minutes.
In your stand mixer, whip together the eggs and buttermilk. Add the vanilla.
Once the cocoa mixture has cooled, slowly had a little bit of the mixture to temper the eggs, whisking constantly. Add the remaining mixture, whisking to combine (this might best be done by taking the bowl off the stand mixer and whisking by hand, then putting it back on to the mixer for the dry ingredients).
Add the dry ingredients in 3-4 stages, mixing well to combine.
Divide batter evenly among lined cups, filling each about halfway full. Bake for about 20 minutes. When done, transfer tins to wire racks to cool 5 minutes; turn out cupcakes onto racks and let cool completely.
For the chocolate ganache, heat the heavy cream until just boiling. Then poor over the chocolate chips in a bowl and let sit for 5-10 minutes. Stir to combine and cool slightly so the mixture thickens a bit.
Core the cupcakes, then dip the tops into the ganache. Place on a tray and chill in the freezer for 10 minutes.
For the whipped cream, make sure your whipping cream is cold and your mixing bowl is clean. I like to chill my mixing bowl as well (I find it helps the process). Whip the cream with a whisk attachment until soft peaks form. Add the sugar and whip a bit more until the peaks are a bit stiffer, but not too hard.
Add 2 tbsp of maraschino cherry juice and the chopped maraschino cherries, whipping to combine. Chill if necessary.
Pipe into the cupcakes after dipping into the ganache.
For the frosting, first heat the cherries over medium high heat until liquid is reduced. Put into a food processor and pulse to chop. Add the butter and 1 cup of sugar, beating until combined. Add the remaining sugar gradually and cream. Transfer to a stand mixer and whip until light and fluffy.
Pipe the buttercream onto the cupcakes, aiming to cover the filling hole (left uncovered). Frosting does not need to go out to the edges--you want the ganache to show.
Dip the maraschino cherries in the heated chocolate and place on wax paper. Chill in the freezer for 10 minutes, then place on top of the cupcakes.
Pat yourself on the back. This is one freaking extravagant recipe!