The Deshler Cocktail is a WWI-era relative of the Manhattan. I’m not a boxing historian, but I’m told the “Deshler” in question was Dave Deshler, an American lightweight boxer in the early years of the 20th century. I know nothing of his boxing, but it seems he was good enough to inspire a well-constructed cocktail, I suppose as homage to one of his victories.

Though the recipe first appeared in Hugo Ensslin’s Recipes for Mixed Drinks (1917), the earliest version I have at hand is from the 1948 edition of Patrick Duffy’s Standard Bartender’s Guide. As Duffy describes it, the Deshler is a charmingly tiny, strictly old-school cocktail, mixed with equal parts of rye whiskey and Dubonnet:

The Deshler Cocktail (Duffy)

  • ½ jigger Rye Whiskey
  • ½ jigger Dubonnet
  • 2 dashes Peychaud bitters
  • 2 dashes Cointreau triple sec
  • 1 piece lemon peel
  • 2 pieces orange peel

Shake well with cracked ice, strain and serve with a twist of orange peel.

This is clearly a member of the Jerry Thomas-era Manhattan family.

The Deshler Cocktail, photo Copyright © 2012 Douglas M. Ford. All rights reserved.
The Deshler Cocktail

Robert Hess presents a modernized version of the Deshler, one that parallels changes in the Manhattan itself, in his Essential Bartender’s Guide (2008). Though still a small drink, Hess’s version is a little bit larger than Duffy’s, and heavier on the whiskey proportion.

The Deshler Cocktail (Hess)

  • 1½ oz rye whiskey (Rittenhouse 100, Wild Turkey 101)
  • 1 oz Dubonnet rouge
  • 2 dashes Peychaud bitters
  • ¼ oz Cointreau
  • 1 lemon twist (in mixing glass)
  • 1 orange twist (in mixing glass)

Stir with ice, strain into a cocktail glass. Express and garnish with orange.

This is the version you’ll usually encounter, and it is a fine improvement—clearly a whiskey drink, not as dominated by the Dubonnet. High-proof ryes like the Rittenhouse and Wild Turkey 101 stand up well to the Dubonnet; with standard 80-proof ryes, I’m inclined to up the proportion of whiskey to 2:1.

Deshler cocktail and Rittenhouse, photo Copyright © 2012 Douglas M. Ford. All rights reserved.But it’s still too sweet for my taste. The twists of lemon and orange in the mix indicate that this is meant to be a fruit-forward drink; Duffy’s recommendation to shake the mix—sort of a self-muddling operation—cements the idea. But Duffy’s reluctance to provide more than 2 dashes of Cointreau signals that he, too, may have been worried about sweetness. Cointreau is a pretty aggressive ingredient, both in its “orangeness,” and its sweetness. My preference is to limit Cointreau to about a barspoon (roughly an eighth of an ounce, or 4 ml). That restrains the sweetness and encourages the fresh fruit oils to come forward in the drink.

In the end, the Cold Glass version looks like this:

The Deshler Cocktail (Cold Glass)

  • 1½–2 oz rye whiskey (Rittenhouse 100, Wild Turkey 101)
  • 1 oz Dubonnet rouge
  • 2 dashes Peychaud bitters
  • ⅛ oz (1 barspoon) Cointreau
  • 1 lemon twist (expressed and added to mixing glass)
  • 1 orange twist (expressed and added to mixing glass)

Stir with ice, strain into a cocktail glass. Express and garnish with orange.

If you’re looking for other cocktails use Dubonnet to advantage, you might check Arnaud’s Special Cocktail. It has a similar structure to the Deshler, but is made with Scotch instead of American whiskey.