I decided to post an entrant into the competition to create a new Hotel Monteleone Cocktail. What I came up with is likely too simple to win the contest, but certainly not too simple to drink.
When I think of New Orleans drinks, I think of rye and absinthe in drinks like the Sazerac and Vieux Carre. But given the 1949 opening date of the Carousel Bar, there probably wasn't much rye being made post-Prohibition. I lead with New Orlean's own absinthe substitute Herbsaint, which I always enjoy with robust fruit and berry flavors. I tried some Poir Williams drinks that just weren't hitting it. Then I tried experimenting with grenadine, absinthe, and gin. That combination was pretty good, but I couldn't get it all the way there. I added an egg white to the mix to froth it up like a Ramos Gin Fizz, and it was yucky.
Then I ran out of grenadine. I did have some POM pomegranate juice though, so I started playing with that. At first I thought I'd make something like an absinthe pomegranate Pimm's Cup, but that was gross. I couldn't make the gin work, and my fizzy mixers- soda water and ginger ale- made the thick juice taste watered down.
In the end, I went with the simplest flavor combination I'd tried all day.
Monteleone Cocktail (Cooler Edition)
4 ounces POM pomegranate juice
1 1/2 ounces Herbsaint
Pour ingredients over ice in a double old-fashioned or rocks glass. Lemon peel garnish optional.