handsome bob

2 oz Bourbon (Old Grand-Dad Bonded)
1/2 oz Cynar
1/4 oz Maraschino (Luxardo)
1/4 oz Pineapple Syrup
2 dash Angostura Bitters

Stir with ice and strain into a cocktail glass.

The discussion of cocktails created in Saratoga Springs, NY, in the late 19th century seemed to focus on the better known Saratoga Cocktail that was published in Jerry Thomas' book and appeared like a precursor of a Vieux Carré since Benedictine and Peychaud's Bitters were all that was added to make that 1930s number. The lesser known Saratoga Cocktail was from Harry Johnson's book that appeared like a brandy Old Fashioned riff with pineapple syrup and Maraschino as the sweeteners. The Maraschino and general structure made me think of the Fancy Free from Crosby Gaige, so when I decided to riff on Johnson's Saratoga, I took the Fancy Free's Bourbon base. Originally, I was considering rum, dry vermouth, and the Saratoga's two sweeteners akin to a rum Brooklyn in structure, but I decided to utilize Cynar instead of vermouth for it worked well with Maraschino in the Bensonhurst and with pineapple syrup in the Tres Piñas and Aguamiel.
For a name, I kept with the discussion of fancy folk in Saratoga Springs and picked "Handsome Bob" after Robert Hillard, a champion dude who ultimately lost to Evander Berry Wall a/k/a the "King of Dudes." In the glass, the Bourbon joined the nutty Maraschino aromas on the nose. Next, malt, caramel, and pineapple on the sip changed into whiskey, funky herbal-nutty cherry, and allspice on the swallow.