The Ward 8 belongs to a fairly small set of cocktail recipes, apparently inspired by political events. The story with this one is that it commemorates the winning of a seat in the Massachusetts legislature by one Martin Lomasney – with the eighth electoral ward being the one to return him the winning margin – at the end of the C19th.
I imagine the election was held in warmer months, as the drink is essentially a sophisticated whiskey sour, made with rye and a mixture of orange and lemon juices, so it’s a cool & refreshing drink, with a gentle alcohol burn from the rye. A small amount of grenadine lends an attractive colour, and acts as the sweetening agent. It’s a little too sour unless you have very sweet orange juice, but I wouldn’t be inclined to add too much grenadine to compensate; it’s slightly too cloying a sweetness & the whole drink could end up tasting like orange boiled sweets without care.
40ml rye whiskey
20ml lemon juice
20ml orange juice
Shake well over plenty of ice & double strain (for the orange & lemon pulp) into a martini glass. Garnish with a single maraschino cherry.