Gary Larry Rayburn was born to Bo and Helen Ferguson Rayburn on April 23, 1983, in Tremont, Mississippi. The family skirted the poverty line, a state of affairs that Gary always wanted to escape but didn't seem to know how.
Teachers remember his academic efforts as inconsistent at best. He did well one year, poorly the next—neither outcome making much of an impression on his parents, who never even bothered to attend parent-teacher conferences. Gary pursued a variety of hobbies—playing the trumpet, building his own car from a kit, and playing football—with reckless abandon and then quit without fanfare, his reasons never clear.
After graduating somewhere in the middle of his class, Gary applied to several colleges but failed to complete the long application process. In the end, he became a roofer for his uncle Matt Ferguson, an alcoholic who ran his Tupelo business partly from a stool in a local bar and partly from the back of his battered van.
Two months into the job, Gary spent six weeks in a body cast after falling off a ladder. Shortly after emerging, Gary tried a new escape route that seemed to meet his needs. He enrolled in a school he learned about from an infomercial, and he earned his Bachelor's degree in General Education while continuing to shingle during the daylight hours. He followed this initial academic success with a law degree from the same correspondence school.
Despite his uncle raising his pay by a dollar an hour, Gary found that prospective employers were not impressed by his academic achievements. He was unable to find new work, despite sending out dozens of resumes with boilerplate cover letters. Gary spent the next five years climbing ladders and swinging hammers.
In April of 2009, Gary was part of a roofing crew sent to the Richard and Connie Pruitt residence. While talking to the owners, Gary learned that he shared a birthday as their son, Robert, who had recently graduated from law school and was now working as an Assistant District Attorney in Yoknapatawpha County.
Connie invited Gary to a birthday party for Robert, and the young men soon became friends. Robert coached Gary through the Multistate Professional Responsibility Exam and the Mississippi Bar Exam, which Gary eventually passed.
Robert also introduced Gary to gambling on sporting events. Gary threw himself into this new hobby and soon found himself losing more than he ever won. Robert is credited with bailing his friend out of several ugly situations.
According to numerous acquaintances, the friendship always had a dysfunctional dynamic. Robert was exactly one year older and more successful in every way than Gary, who is often described as little more than a wannabe. Gary's mother said she "never liked that Pruitt boy" who made her son miserable so he could feel better.
In 2011, Robert worked out a deal with his boss where Robert would take two weeks without pay so Gary could be hired at Robert's salary during that period with the understanding that Robert would still do the work. This arrangement allowed Gary to say he'd been an Assistant District Attorney and Robert's boss to finally fix his leaky roof at no personal expense.
Soon afterward, Robert and Gary went into private practice together. Robert did the legal work, and Gary did whatever else needed to be done that couldn't be delegated to their secretary, Mira Lee. At Robert's urging, Gary volunteered for local Habitat for Humanity projects, borrowing his uncle's van to haul materials and donating his roofing skills, and thereby raised the small law firm's profile in the community.
Gary was grateful for all Robert had done for him, but over time, he began to chafe at his dependence on Robert's largesse. According to his Uncle Matt, while Gary may have moved up in the world when he traded his hammer for a desk, now he was "working on" something even better: Robert's ex-wife, attorney Gloria Bell. Gary was determined to succeed somewhere Robert had failed, even if he couldn't afford to let his partner know what he was doing.
Gary also tried to top his partner through friendly wagers. As Gary made one bad choice after another, however, the bets became less friendly. This culminated in a bet on the St. Louis Cardinals vs. Chicago Cubs baseball game of July 9, 2021.
According to several sources, Gary bet Robert that the visiting team would score the first run. If Gary won, Robert would forgive all outstanding debts. If Robert won, Gary would owe his partner double the standing amount.
The Cubs scored the first run.