Gary Larry Rayburn was born to Bo and Helen Ferguson Rayburn on April 23, 1978, 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 — including 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 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.

Gary spent six weeks in a body cast after falling off a ladder two months into the job. Shortly after emerging, Gary tried a new escape route: one that seemed to meet his needs. He contacted a school he learned about from an infomercial and enrolled in their correspondence classes. He earned his Bachelor's degree in General Education while continuing to shingle during the daylight hours. Gary followed this initial academic success with a law degree conferred onto him by 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 and he was unable to find new work, despite sending out dozens of resumes with form cover letters. Gary spent the next five years climbing ladders and swinging hammers.

In April of 2004, Gary was sent as part of a roofing crew to the residence of Richard and Connie Pruitt. While talking to the owners on his break, Gary learned that he shared the same 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 attacked this new hobby with his customary reckless abandon 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 hanger-on, a wannabe. Gary's mother, Helen, said she "never liked that Pruitt boy" who made her son miserable so he could feel better.

In 2006, Robert worked out a deal with his boss where Robert would take two weeks without pay so that Gary could be hired at Robert's salary during that period with the understanding that Robert would still do the work. This allowed Gary to claim he'd been an Assistant District Attorney and Robert's boss to finally fix his leaky roof at no personal expense.

Soon afterwards, 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.

Both Gary's obvious desire to emulate Robert and his continued dependence on his friend apparently calmed Robert's feelings of insecurity. Yet for all the reasons that Gary worshipped Robert, he also resented him. According to his Uncle Matt, Gary may have moved up in the world when he traded his hammer for a desk, but now he was "working on" something even better: Robert's ex-wife, attorney Gloria Bell. Gary was determined to succeed somewhere that 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 and less friendly. This culminated on a bet regarding the Florida International University (FIU) vs Old Miss baseball game of February 19, 2016.

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.

Ole Miss scored the first run.

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