“Behind the eight ball” (in a troublesome situation)

To be “behind the eight ball” is an expression from the game of pool meaning to be in an awkward position or out of luck. The expression actually comes from “kelly pool” and not the game of “eight-ball” itself (that did not become popular until after the expression was famous).
   
“If Charley Heins doesn’t stop buying stocks he may wind up behind the eight ball” was printed in the Buffalo (NY) Evening Times on September 25, 1923. “The Phillies ended their season up ‘behind the eight ball,’ as the vulgar saying goes” was printed in the Hamilton (OH) Evening Journal on August 19, 1926.
 
 
Wikipedia: Kelly pool
“Behind the eight ball”
“Behind the eight ball” (or “behind the eight”) is a common idiom meaning to be in trouble, stymied or thwarted, in an awkward position or out of luck. It is often assumed that the expression derives from the inability to use the 8 ball in a combination in the game of eight-ball—if the cue ball is directly behind the 8 ball a player has no direct shot route. However, numerous billiards-specific and etymological publications state that the expression derives instead from kelly pool, or an early version of kelly pool called kelly rotation.
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Thus, multiple-time world champion Steve Mizerak explains that behind the eight ball cannot derive from the game of eight ball as “the phrase predates the game ... by at least 20 years.”

Two different kelly pool-based derivations for behind the eight ball are provided in diverse sources. As noted, in kelly pool each player is randomly assigned a specific ball of the fifteen ball rack, which must be made in numerical order. The game ends when any player makes his assigned ball. Based on these rules, one origin theory holds that when a large number of players are participating, players assigned balls numerically higher than 8—that is, balls that are behind the 8 ball in order—have little chance of winning. This is a result of the likelihood that random distribution will result in multiple players with assigned balls numbered lower than 8 having an opportunity to shoot first, and that with such large a number of players at least one will come to the table with the opportunity to shoot at his assigned ball.
 
A second theory refers to a kelly pool rule variation under which the 8 ball is excluded from assignment as a secret number and, if another ball strikes the 8 ball at any time during play, the player responsible is penalized. “So a position directly behind the eight ball is a position of great hazard.”
 
(Oxford English Dictionary)
eight ball | eight-ball | eightball, n.
U.S.
a. The black ball, numbered eight, in the North American variety of pool (pool n.3 2); this variety of pool.
1932   World’s Work Feb. 26/1   Mr. Ells, the wizard of the cue, in a position he expertly diagnosed as squarely behind the 8-ball.
b. behind the eight ball, at a disadvantage; ‘snookered’.
1932 Behind the 8-ball [see sense a].
1934   J. O’Hara Appointment in Samarra (1935) 12   You get signing checks for prospects down at the country club, and you wind up behind the eight-ball.
       
25 September 1923, Buffalo (NY) Evening Times, “The Daily Hammer,” pg. 11, col. 7:
If Charley Heins doesn’t stop buying stocks he may wind up behind the eight ball.
 
19 August 1926, Hamilton (OH) Evening Journal, “On ‘the Trail’ of Sport,” pg. 10, col. 1:
The Phillies ended their season up “behind the eight ball,” as the vulgar saying goes.
 
18 October 1926, The Evening News (Harrisburg, PA), “Runyon Says” by Damon Runyon, pg. 19, col. 4:
But Herrera was no hand for training, and he wound up behind the eight ball, as the boys say.
 
23 December 1926, Brooklyn (NY) Times, “Sportopics” by James J. Wood, pg. 2A, col. 4:
Those with ideas to the contrary usually wind up behind the eight-ball, as they say in the better class clubs.
   
20 January 1928, Brooklyn (NY) Daily Times, “Still a World for Hoppe to Conquer” by John A. Lewy, pg. 1A, col. 2:
Facing none other than our friend Augie Kleckhefer at the Strand Academy, Willie found himself behind the 8-ball, as the boys say.
 
Google Books
The Young Manhood of Studs Lonigan
By James Thomas Farrell
New York, NY: The Vanguard Press
1934
Pg. 102:
“Jesus, he’s one poor bastard who ended up behind the eight ball,” Slug said.
   
Google Books
Never Mind the Lady
By David Garth
New York, NY: Dodd, Mead
1935
Pg. 107:
“Listen,” the girl was saying spiritedly, “I left a six here and you can’t put me behind the eight ball with Snake Eyes. A woman has some rights, you pirates.”
   
OCLC WorldCat record
Behind the 8-ball!.
Author: Nell Crawley
Publisher: New York ; London : [publisher not identified], 1942.
Edition/Format:   Print book : Fiction : English
 
Urban Dictionary
behind the eight ball
In a bad situation, in a losing position.
The phrase comes from pool (or billiards). When the cue (white) ball is behind the eight (black) ball, a player usually has no shot.
I’m really behind the eight ball at work. I have too much work to do but we can’t afford to hire anyone to help out.
by VAKI5 May 11, 2005