Green Hat Cocktail

George Cassiday - bootlegger for Congress

Your cocktail calendar entry for: April

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We’re mixing the Green Hat cocktail on April 12 for the birthday of The Man in the Green Hat, George Cassiday.  Who was George Cassiday, you ask?  He was Congress’ primary bootlegger during prohibition, from 1920 to 1930.  That’s right, he and friends supplied booze to at least 80% of the lawmakers of the time.  That certainly puts him in our Hall of Fame.

It seems the lawmakers who voted for Prohibition were in the “do as I say not as I do” camp.  Unlike our current legislators, of course….oh, wait.  Nevermind.

George Cassiday

George Cassiday was born April 12, 1892 and went on to serve in World War I.  He tried going back to his pre-war job at the Pennsylvania Railroad but didn’t re-qualify.  He fell into bootlegging after a friend told him that booze was bringing good prices on Capital Hill and that he could make a living.

Cassiday would get his booze in New York or Philadelphia and return with two suitcases weighed down by 40 quarts of booze.  Problems sometimes occurred, with a passenger in Penn Station once wryly noting, “Say, buddy, your clothes are leaking.”

Cassiday operated from the House Office Building from 1920-1925.  Customers were easy to find but meeting demand was tough as he could only carry in as much as he could hide in his coat.  One day a Midwestern congressman had an idea, figuring it would help if he had a dedicated location.  So Cassiday was given space in the House Office Building.

Nonetheless, Cassiday was arrested in 1925 when entering the building with bottles in a briefcase.  He never left home without a hat and was wearing a green hat at the time, so he earned the nickname of The Man in the Green Hat.

Cassiday was barred from entering the House, but he had a simple solution:  move to the Senate.   He had decided senators were more careful than representatives and this worked well for another five years.  After another arrest in 1930 he was sentenced to a year in jail.

He never actually spent a night in jail, instead signing himself in every morning and out every night.  Cassiday agreed to stop bootlegging but went on to write a series of articles for The Washington Post.  He told the whole story but never named names and passed away in 1967.

Green Hat Cocktail

The Green Hat cocktail is an obvious choice for George Cassiday’s birthday but it’s not only because of the name.  It has more going for it.

The Green Hat is a variation on the Old Fashioned, the most classic of cocktails and about the best thing you could do with whatever whiskey you got during Prohibition.  Thinking Old Fashioned also means it uses bitters, which were still available during Prohibition.  Bitters, you see, are considered medicine so they got around the wrath of the temperance zealots.

The only real modification from the classic Old Fashioned is the addition of a teaspoon of Chartreuse.  As we’ve talked about on World Chartreuse Day, the eponymous liqueur was conceived as a medicine.  Little known is that during Prohibition your doctor could write you a prescription for medicinal alcohol.  You can do the math.  It’s how drinks like the Last Word came into existence.

The origin of the Green Hat cocktail is a mystery, it seems to be one of those things that spontaneously occurred somewhere in the bar world and diffused from bar to bar.  It’s also ridiculously simple to prepare as you build it right in the glass, without any bar hardware to wash afterwards.

green hat cocktail

Green Hat Cocktail

The Green Hat cocktail is a rye whiskey Old Fashioned with one simple modification: a small float of Chartreuse added. There's no known history of this particular drink, it seems to have occurred spontaneously. But that's no surprise when you consider just what Chartreuse can do for a drink. With its highly complex flavors, which play well with any whiskey, it's hard to make a drink where adding a bit of Chartreuse doesn't work at all. Highly recommended, it's simple to make as it's simply built in the glass.
5 from 1 vote


  • Old Fashioned Glass



  • Build drink in the glass.
    Add ice (preferably one large cube, whiskey, bitters and simple syrup. Stir to combine.
  • Float teaspoon or Chartreuse on top.
  • Express twists and garnish glass.
  • Drink.
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2 Comments. Leave new

  • craig a nelson
    April 12, 2023

    5 stars
    I might have done better in History class had it included stories like these.
    Gonna order one tonight!

  • I used to take a bus through Anacostia, Washington DC way back in the 60s along what is now ML King Jr Avenue and wondered about a bar I passed called The Man In The Green Hat. Thanks for this!


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