Stuti Gokhale
In August 1996, Jeffrey Wolfe and his girlfriend traveled from Houston, Texas, to Jackson County, Mississippi, to collect some debts. But in what seemed like a drug deal gone wrong, Jeffrey was brutally murdered, as his horrified partner witnessed. Investigation Discovery’s ‘Shattered: The Box’ explores the shocking events of this gruesome case and how the killers were finally brought to justice. So now, let’s delve into the details, shall we?
How Did Jeffrey Wolfe Die?
Born in November 1974, Jeffrey Wolfe lived in Houston, Texas, and worked as a marijuana dealer. He began dating 18-year-old Charlene Leaser around August 8, 1996, and just three days later, he introduced her to his father. The next day, the young couple departed for Moss Point, Jackson County, where 21-year-old Jeffrey was supposed to collect some debts for a drug deal. However, on August 13, 1996, the police received a call from a woman in Moss Point claiming he had been shot dead.
Upon arriving, they found a petrified Charlene at the woman’s house, stating that she had been raped and that Jeffrey’s body had been dismembered and scattered in a nearby bayou. Following this lead, the police rushed to the alligator-infested creek and managed to retrieve around 80 percent of his body parts, including his severed head. Moreover, the rest of the body parts contained bullet casings, indicating that the cause of death was indeed gunshots.
Who Killed Jeffrey Wolfe?
Charlene told the authorities that she and Jeffrey had come to Moss Point to meet a butcher named Gary Simmons and his former brother-in-law, Timothy Milano. Both men used to sell marijuana for her boyfriend; while Jeffrey or his representative would drop off the consignment to Gary, the latter and Timothy would then sell it around and give the payment to the 21-year-old. On August 12, 1996, Jeffrey and Charlene drove to Gary’s house to collect one such pending payment ranging between $12,000 and $20,000.
Things were amicable when the couple arrived at Gary’s residence, but when he stated that he did not have the money, it led to a heated argument in the wee hours of August 13, 1996, ending with Timothy fatally shooting Jeffrey with a .22 caliber rifle. Charlene heard the gunshots and saw him fall, though before she could react, Gary allegedly grabbed her and dragged her into a back room, where he tied her with a rope and shut her in a foot locker. She managed to untie herself twice, but then he sexually assaulted her before tying her again and locking her in the metal box.
Gary then returned to the living room and dragged Jeffrey’s body into the bathroom, where he dismembered it using two butcher knives he had sharpened at work. Afterward, he and Timothy carried the victim’s remains in two buckets to the nearby bayou in several trips, dumping them for the alligators to feed on. They then came back and cleaned Gary’s house and left, after which Charlene managed to escape from the foot locker, got dressed, and ran to the neighbor’s house, who then alerted the police.
When the officers arrived, Charlene took them to Gary’s house, where they found the knives and some of Jeffrey’s remains in the yard. After finding the rest of the body in the bayou, they proceeded to arrest Timothy from his apartment. Meanwhile, Gary went to his former wife’s house and made a video confession, vaguely describing what he had done; he turned himself in a day later. Both he and Timothy were charged with counts of kidnapping, rape, and capital murder.
Where Are Gary Simmons and Timothy Milano Now?
In August 1997, Gary Simmons was convicted for Jeffrey’s murder and the kidnapping and rape of Charlene. He was given a life sentence for the latter two charges and awarded the death penalty for the murder charge. He remained incarcerated for around 15 years till he was executed by legal injection on June 10, 2012, at the Mississippi State Penitentiary in Parchman, Mississippi.
Timothy Milano was found guilty of the murder and kidnapping, but the rape charge was dismissed in July 1998. He was sentenced to life behind bars and is currently incarcerated at the Central Mississippi Correctional Facility in Pearl, Mississippi.
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