The Butcher and the Box: Gary Simmons' 1996 Crimes

On August 13, 1996, in Moss Point, Mississippi, a debt collection visit turned into one of the state's most brutal crimes. What began as a transaction over money owed would culminate in murder, sexual assault, torture, and dismemberment—a case that would eventually lead to Mississippi's 21st execution in the modern era.

Gary Carl Simmons Jr. was a butcher by trade, working at a local grocery store. That August day, 21-year-old Jeffrey Wolfe and his girlfriend Charlene Brooks visited Simmons' property over a disputed debt—accounts suggest between $1,000 and $20,000 related to drugs. When Wolfe arrived with only $1,000, Simmons was furious. The disagreement escalated into violence.

Timothy Milano, Simmons' accomplice, fatally shot Wolfe with a .22-caliber rifle during their argument. But Wolfe's death was only the beginning of a nightmare that would last approximately two days.

Simmons turned his rage toward Brooks. He hog-tied her, locked her inside a foot locker—essentially a large trunk—and held her captive. During her confinement, he raped her repeatedly, threatening her with chilling clarity: her life depended on how well she performed sexually. The psychological and physical torment was designed to break her will to resist or escape.

Meanwhile, Simmons used his professional expertise in the most grotesque way imaginable. In his bathtub, he dismembered Wolfe's body using work knives—tools of his butcher's trade now instruments of desecration. After gutting the corpse, Simmons and Milano scattered the remains in the alligator-infested bayou behind the property, likely believing the swamp would destroy all .