"Irish handcuffs” is a slang term to describe having an alcoholic drink (such as a pint of Guinness) in each hand. “I spy him across the crowded room wearing Irish handcuffs, which of course means holding a glass of beer in each hand” was cited in print in 1997.
Both drinks don’t have to be beer—one hand could have a shot of whiskey. “Irish handcuffs: saloon slang; a beer and a shot” was cited in print in 1999. “Irish Handcuffs— that’s a pint in one hand and a whiskey in the other” was cited in 2009.
Google Books
The Reluctant Pornographer
By Bruce LaBruce
Toronto, Ont.: Gutter Press
1997
Pg. 171:
I spy him across the crowded room wearing Irish handcuffs, which of course means holding a glass of beer in each hand, one of which he shoves into my hand when I approach him, along with his tongue down my throat.
Google Books
How to Be Irish
(Even if You Already Are)
By Sean Kelly and Rosemary Rogers
New York, NY: Villard Books
1999
Pg. 74:
Irish handcuffs: saloon slang; a beer and a shot.
16 March 1999, New York (NY) Post, “It’s good for what ales you,” pg. 50:
It’s also famous for the legendary owner Stevie Duggan, who’s liable to put you in a set of Irish handcuffs—a pint of Guinness in each hand—if you become a regular.
SpaceBattles Debate Forums
What do you call two full beers occupying both hands of a person?
Irish handcuffs.
(...)
spacejozilla, Aug 23, 2001
Google Groups: rec.music.makers.songwriting
Newsgroups: rec.music.makers.songwriting
From: 60 cycle hum
Date: Sun, 14 Mar 2004 13:42:51 -0600
Local: Sun, Mar 14 2004 1:42 pm
Subject: Re: HAPPY ST. PAT’S DAY!
I’ll have irish handcuffs on that day
you know, a beer in each hand 
Urban Dictionary
Irish handcuffs
when a person is carrying an alcoholic beverage in both hands at the same time.
Hemish O’Maley was in Irish handcuffs last night at the pub. He always had a Guinness in each hand.
by jonesy Jun 23, 2004
To Serve Mankind
August 3, 2008
Bar and Restaurant Lingo
(...)
COMMENTS
Grady S says:
Irish Handcuffs- a guy holding two beer so he cannot fight, or throw a punch
November 17, 2011 at 12:23 pm
Google Books
Esquire: The Magazine for Men
Volume 152
2009
Pg. 66:
And we shake off the Irish Handcuffs— that’s a pint in one hand and a whiskey in the other, for those of you who only drink at the fancy cocktail bars— and switch to one-handed drinking when the angle of the little hand starts getting acute.
Above, a 1934 plaque from the Big Apple Night Club at West 135th Street and Seventh Avenue in Harlem. Discarded as trash in 2006. Now a Popeyes fast food restaurant on Google Maps.
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Above, Big Apple Corner at 54th Street and Broadway in Manhattan. Google Maps.
Above, John J. Fitz Gerald, from the Aug. 15, 1931, Binghamton (NY) Press, pg. 14.
Listen to Robert Emmerich introduce "The Big Apple," a hit song from 1937. Music written by Bob and performed by Tommy Dorsey's Clambake Seven with Bob on piano. Lyrics written by Buddy Bernier and sung by Edythe Wright. Audio provided by Dorothy Emmerich.
Also listen to a 1937 "The Big Apple" song by Ozzie Nelson and his Orchestra. See a 1929 photo of John J. Fitz Gerald and a 1931 photo of John J. Fitz Gerald.
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