The Bookie Pool concept originated in the hallways of McDATA Corporation, the result of massive, awe inspiring brain activity churned out by Dick Cooley, Jeff Mitchem, Mike Tatum, and Fred Williams. With a bold membership of 12, the Bookie Pool launched its inaugural season in 1992.

The following year, after eating a burrito at La Cabana, Jeff Mitchem suggested implementing a plus 7 rule which would give losers the chance to get back into the race with a double the return on their wager. After finishing his taco, Fred concurred and quickly instituted the new sucker bet, er, rule into the pool. The following year it was officially changed to the plus 6 rule. Despite the persistent pleas of Pat Mundy, a plus 18 rule to quadruple one's bet has yet to generate serious consideration.

Pool membership has steadily increased each year with very little turnover, despite the complete domination of pool operator Fred Williams, who continues to pummel rookies and veterans alike.