The expressions “holding all the cards” is derived from playing cards and means to have an advantage. “Ever notice, when finally you’ve got to a position where you’re holding all the cards, that everybody else is playing chess?” was cited in The Wall Street Journal in 1988 and became a popular joke on the Internet and in newspapers by 1999.
 
   
IFindKarma.com
@Sender: Henry Cate III:OSBU North:Xerox
Date: 21 Nov 88 13:50:53 PST (Monday)
Subject: Life 3.R
From: Cate3
To: Cate3
(...)
From The Wall Street Journal today:
 
Ever notice, when finally you’ve got to a position where you’re holding all the cards, that everybody else is playing chess?
 
The Good Clean Funnies List
Bumper Sticker Philosophy
Date: Sent Monday, June 29, 1998
(...)
When you’re finally holding all the cards, why does everyone else decide to play chess?
 
13 February 1999, The Salt Lake Tribune (Salt Lake City, UT), “Having Trouble With the Original 10 Commandments? Try a Few of These to Live a Better Life” by Robert Kirby, pg. C1:
When you’re finally holding all the cards, why does everyone else turn out to be playing chess?
 
16 April 1999, Paris (TX) News, “Weekender” by Gary Lawson, pg. 1B, col. 6:
When you’re finally holding all the cards, why does everyone else decide to play chess?
   
Google Groups: alt.pizza.delivery.drivers
Bubba5737
5/2/99
(...)
When you’re *finally* holding all the cards,
why does everyone else decide to play chess ?
 
Google Books
Net-Wit.Com:
A Smorgasbord of E-Mail and Internet Wit Blended With Humorous Incidents from the Author’s Wild and Wooly Life
By Marv Rubinstein
Rockville, MD: Schreiber Publishing
2000
Pg. 153:
When you’re finally holding all the cards, why does everyone else decide to play chess?
 
Google Books
The Almost Wet Your Pants Book of Humor
By R. Bruce Baum
Bloomington, IN: AuthorHouse
2010
Pg. 2:
When I’m finally holding all the cards, why does everyone decide to play chess?