Jeffrey Wolfe Murder: Capture, Trials, and Simmons’s Execution

The Jeffrey Wolfe murder was the August 1996 killing of a 21-year-old Texas marijuana dealer, Jeffrey Wolfe, at a home in Moss Point, Mississippi, over an unpaid drug debt. Gary Carl Simmons Jr., a grocery-store butcher, and his brother-in-law Timothy Milano shot Wolfe, dismembered his body, and dumped the remains in a bayou. Simmons also kidnapped and repeatedly raped Wolfe’s 18-year-old girlfriend, Charlene Brook Leaser, before she escaped and led police to the scene. Simmons was sentenced to death and executed by lethal injection on June 20, 2012. Milano received life in prison without parole and remains incarcerated in Mississippi.¹²

What Happened on August 11–12, 1996

Wolfe dealt marijuana out of the Houston area and had fronted drugs on consignment to Simmons and Milano, who ran a small operation out of Simmons’s home in the Kreole community of Moss Point. By the summer of 1996 the pair owed him somewhere between $12,000 and $20,000.¹³

On Sunday, August 11, 1996, Wolfe drove from Texas to Mississippi with Leaser, his girlfriend of three days, planning to collect the debt and then continue on to New Orleans. His father Paskiel later said Jeffrey had received a note inviting him to visit Milano in Moss Point.²³

Simmons and Milano did not have the money or the drugs. When the couple arrived late that night, an argument broke out in the kitchen of Simmons’s home, and Milano shot Wolfe multiple times with a .22-caliber rifle. Leaser testified that she saw Milano standing directly behind Wolfe holding the rifle when the shots were fired.¹²

Evidence at trial pointed to planning rather than a confrontation gone wrong. Simmons, a butcher at a local grocery store, had brought his professional knives home that weekend, something he did not usually do, and had borrowed a boat from a neighbor shortly before Wolfe’s arrival. The two men had expected Wolfe to be carrying as much as $20,000 in cash but found only about $1,000.¹³

After the shooting, Simmons used his butcher knives, bolt cutters, and a bush hook to dismember Wolfe’s body in a bathtub, severing the head, limbs, and organs. He and Milano loaded the pieces into buckets and used the borrowed boat to scatter roughly 126 pounds of remains into a bayou behind the property, making several trips. Simmons reportedly believed alligators would consume the evidence. Police later recovered about 80 percent of the body, including the head, arms, fingers, organs, and a torso containing bullet casings.⁴³

While Wolfe was being killed and cut up, Simmons turned on Leaser. He hog-tied her, stripped her, and locked her inside a custom-built metal footlocker, removing her periodically over the following hours to rape her while threatening her life. Simmons later told an acquaintance, Dennis Guess, that he had kept her in a box to “train her” and intended to make her a “sex toy.” Milano, according to testimony at trial, declined Simmons’s offer to rape Leaser as well.⁴²¹

How the Killers Were Caught

While Simmons and Milano were out on the bayou disposing of the remains, Leaser kicked open the lid of the footlocker and got out of the house sometime after 6:00 a.m. She ran to a neighbor, who called police. Officers went to the Simmons residence and found bloody buckets and other evidence, then recovered Wolfe’s remains from the bayou.³²

Milano was arrested first, at his apartment in Pascagoula. Simmons fled to Mobile, Alabama, went to his ex-wife’s home, and recorded a videotape addressed to his family in which he said, “I can’t make it undone.” He turned himself in a day or so later. He also confessed to Dennis Guess that he had “whacked a drug dealer” and “deboned him” because the dealer had come to collect a debt.³²¹

On October 11, 1996, a Jackson County grand jury indicted both men for capital murder, kidnapping, and rape. The trials were severed.¹

The Trials and Sentences

Simmons went first. His trial began August 25, 1997, in Jackson County Circuit Court before Judge Bill Jones, with jury selection moved to Lauderdale County on a change of venue. On August 29, 1997, the jury convicted him of capital murder, kidnapping, and rape. He was sentenced to death by lethal injection for the murder and to two consecutive life sentences for the kidnapping and rape.²¹

Milano’s trial began July 27, 1998, before Judge Edwin C. Hardin, with District Attorney Keith Miller prosecuting. The rape charge against him was dismissed on the morning of trial. He was convicted of capital murder and kidnapping and sentenced to life without the possibility of parole for the murder, plus a consecutive 30 years for the kidnapping.⁵⁶ Milano was 19 at the time of the killing.⁷

Appeals and Simmons’s Execution

On direct appeal, Simmons argued among other things that he should have been allowed to raise self-defense or manslaughter because Wolfe had allegedly “broke bad” during the confrontation. The Mississippi Supreme Court rejected that on December 13, 2001, pointing to the extensive evidence of premeditation, and affirmed every conviction and sentence. The U.S. Supreme Court declined to hear the case in 2002. State post-conviction relief was denied in 2004. A federal habeas petition was denied by the U.S. District Court for the Southern District of Mississippi in 2008, and the Fifth Circuit affirmed on August 30, 2011, finding that although one aggravating circumstance had been “improperly applied,” the error was harmless.¹²⁸⁹

Milano’s own appeal ended on April 26, 2001, when the Mississippi Supreme Court affirmed his convictions, holding that although the aiding-and-abetting jury instructions were technically erroneous, the error was harmless because other instructions correctly required proof of every element beyond a reasonable doubt.⁶

Simmons was executed by lethal injection at the Mississippi State Penitentiary in Parchman on June 20, 2012. He was 49. Last-minute appeals to the U.S. Supreme Court and the Mississippi Supreme Court failed, and Governor Phil Bryant declined to intervene. His final statement, in part: “I’ve been blessed to be loved by some good people, by some amazing people. I thank them for their support. Now, let’s get it on so these people can go home.” He was pronounced dead at 6:16 p.m.¹⁰²

Wolfe’s father Paskiel and stepmother Linda watched the execution from the witness room. Paskiel called it “16 years overdue” and said he would visit his son’s grave to “tell him justice had finally been served.” Both were angry that Simmons had offered no apology.²

Where the Case Stands Now

Timothy Milano is still in prison. As of October 2025, Mississippi Department of Corrections records listed him at the Central Mississippi Correctional Facility, serving life without parole for capital murder and the consecutive 30-year sentence for kidnapping.¹¹

Charlene Brook Leaser, now known as Brook Weber, changed her name and appearance and spent years, by her account, “running and hiding” out of fear of retaliation from Simmons’s family. In February 2024, the Investigation Discovery series Evil Lives Here aired an episode titled “Butcher and the Box” featuring Weber, then 45, and Simmons’s ex-wife, Lori Lucas. Lucas, who had testified in Simmons’s favor at his 1997 sentencing, said in the documentary that Simmons had physically abused her, including choking her unconscious, and alleged that he had abused her stepchildren and molested their daughter. She also said she had found binders of his writings describing fantasies of torturing women and keeping sex slaves, including a story about imprisoning a woman in a locked box, echoing the footlocker used to hold Leaser. Weber’s response: “She could have stopped him, and she didn’t. I knew he was a monster, and it only took me one night to figure that out — all of that could have been prevented if someone had just taken a stand.”¹²

1
Findlaw. Simmons v. State, No. 97-DP-01550-SCT
2
Clark County Prosecutor. Gary Carl Simmons Jr.
3
GulfLive. Horrifying Murder, Rape Case Revisited
4
Primetimer. 5 Horrific Details About the Murder of Jeffrey Wolfe
5
Mississippi Supreme Court. Milano v. State, No. 1999-KA-00097-SCT
6
Findlaw. Milano v. State, No. 1999-KA-00097-SCT
7
UPI. Texas Man Found Dismembered in Miss.
8
Findlaw. Simmons v. State, Post-Conviction Relief
9
vLex. Simmons v. Epps, 654 F.3d 526
10
The Mississippi Link. Man Executed for Killing and Butchering Drug Dealer
11
Mississippi Department of Corrections. Inmate Details – Timothy Milano
12
GulfLive. New Documentary Butcher and the Box Chronicles Mississippi’s Haunting Case