On November 3, 1998, eight-year-old Madelyn Rae Clifton arrived home from school in Jacksonville, Florida. She practiced some piano before heading outside to play.
It was another routine day in the Lakewood neighborhood, where houses sat so close together that kids moved freely across neighbors’ yards.
Maddie’s plan was to play out her afternoon, and her comfort with outdoor sports had even earned her a reputation as a tomboy. Her first stop was down the street to hit golf balls with her neighbor, Larry Grisham, then coax a teen neighbor, Joshua Phillips, into a game of basketball, and then head back home for dinner.
While she was at the Phillips driveway, an elderly woman who lived nearby watched Joshua creep up on Maddie and startle her.
She watched them for a few moments, decided it was harmless play, and went back inside. Unfortunately, this is where things took a dark turn.
Phillips later claimed to have accidentally hit her in the eye with the ball while they were playing. She started bleeding and screaming for help.
He immediately panicked, afraid of how his father would react if he came home and found Maddie in that condition. The teen dragged Maddie into the house and into his bedroom.
During the same confession, he said her shorts and underwear came off during the dragging. At that point, he hit her with a baseball bat to stop the screaming, then stabbed her with a pocket knife.
Phillips then hid the body under the base of his waterbed in an attempt to conceal the evidence. When he heard Maddie moaning again, he pulled her out and stabbed her until she stopped making sounds.
At 6.20 pm, Maddie’s mother, Sheila Clifton, called her daughters in for dinner. Maddie’s sister Jessie came in alone and said she hadn’t seen her. Sensing immediate danger because Maddie wasn’t known for staying out late, Sheila ran outside and began knocking on neighbors’ doors, searching for her daughter.
She had no way of knowing her daughter’s body lay lifeless less than a hundred feet away under a teen neighbor’s bed.
The Search Escalates
Her husband, Steve Clifton, arrived home from his job at the local metal shop and immediately joined the frantic search of the yards and driveways. Realizing Maddie was evidently missing, Sheila called emergency services.
The first Jacksonville Sheriff’s Office cruisers arrived at the scene within minutes. They set up a localized command post and began standard missing child protocols, treating it as a potential child abduction site.
By 7.30 pm, officers had begun the initial door-to-door interviews with immediate neighbors. They also spoke with the Phillips family, unaware that Maddie’s body was hidden underneath their son’s waterbed.
A large volunteer search party was formed in the hour. Armed with flashlights, the neighbors broke into small groups and combed through the nearby woods.
Joshua Phillips and his parents, Steve and Melissa, walked across the street and joined in the search groups. Witnesses later said that Joshua acted completely normal, walking alongside the Cliftons as they searched for their daughter.
Days following the initial search, the search escalated to national status, and the FBI was called in to assist the Jacksonville Sheriff’s Office. The search exploded in scale, utilizing helicopters, volunteers, and dogs.
The neighbor’s grandmother did come forward to police, telling them she had seen the Phillips boy with Maddie. When detectives initially questioned Phillips, he freely admitted seeing Maddie.
He claimed they played basketball for a bit before she went back to hitting golf balls or back home. Because he acted calmly and even volunteered to search for the girl, they ruled him out and focused on other leads.
The media frenzy was because it was an election period and crews were already heavily deployed in the area. This case also preempted local election broadcasts, turning the girl’s disappearance into a news event.
The Cliftons lived inside a search that widened by the hour and produced no leads. Maddie’s elder sister, Jessie, was thirteen at the time.
Years later, she described the numbness during that period to Action News Jax, saying, “I remember walking into the IHOP and seeing a missing-persons poster on the window, walking into the restaurant, thinking this isn’t happening, this is not real, we’re going to find her. I was in denial. I wanted to rip it down; I wanted to keep it up.”
A $50,000 reward was also advertised and doubled as the search for Maddie grew. Over the next six days, police actually entered the Phillips home three separate times as part of the routine check.
Because Joshua’s room was heavily cluttered and, as his mother claimed, his pet birds usually gave off an unusual smell, the investigators failed to detect decomposition. Jacksonville patrol sergeant Tom Hackney was among the officers who spoke with Joshua Phillips in his bedroom, where the body of Melissa was concealed.
Hackney told News4Jax, “He was cool as a cucumber. He was absolutely not shocked. Our engagement with him was actually in the bedroom where she was recovered, and he sat on the bed, petting his dog, and just was as unemotional, unaffected by law enforcement being in his house. It’s chilling, thinking about it now.”
The Wrong Man
During the week-long search, police increasingly began to focus on Larry Grisham, the 45-year-old neighbor who played with Maddie before she went missing. Grisham was known among the neighborhood families because he frequently played golf with the children.
On the afternoon of November 3, he happened to be hitting golf balls with Maddie. Grisham said she eventually left to go home and get more golf balls, but it also made him the last known adult point of contact.
Investigators doing background checks discovered that Grisham had a lengthy record of 29 previous arrests. These included two arrests on charges of sexual battery. Though they were dropped, it was a red flag and made him a prime suspect for the perceived abduction.
Detectives hauled him in for a round of questioning. Over that week, they questioned him at least 20 times. According to a Scribd piece, he said, “I am a prime suspect. I am 45 years old, I play with children, and I have a criminal record. That makes me a suspect.”
In addition, Grisham took and failed a polygraph issued by the police. Convinced that he was hiding something, investigators executed arrest warrants and searched his home nine different times. He also complied with a demand to provide DNA samples.
Despite everything that was happening, Grisham stubbornly maintained his innocence, providing a strong alibi for the exact time of Maddie’s disappearance. JSO investigators verified these claims, forcing them to change focus and consider other suspects.
Melissa Phillips’ Discovery
On November 20, 1998, seven days after Maddie went missing, Melissa noticed some fluid pooling near the base of her son’s waterbed. She assumed that it was a leak, but there was also an overpowering stench that felt significantly stronger than bird excrement.
She pulled the baseboard to inspect and found a small white foot.
Horrified by what she had just seen, Melissa let go of the frame and ran out of the house in panic. She flagged down a Jacksonville Sheriff’s officer who was patrolling the neighborhood and ushered the officers into the house.
She later told CBS News, “I just pointed to where they needed to look. I couldn’t even go in.” The police opened the bedroom door and saw two small feet in white socks extending from beneath the waterbed frame.
Tape was scattered nearby, fluid pooled on the floor, and a strong odor filled the room. They immediately sealed it off as a crime scene.
Maddie’s remains were found under the waterbed. Her shirt was pulled up, and her underwear was set beneath her.
A search of Phillips’s rooms also uncovered several air fresheners, rolls of tape, a knife tool, and a baseball bat hidden behind a dresser. Across the street, the Clifton’s watched in horror as the police stretched crime scene tape around their neighbor’s house.
Sheila described the moment that officers came to give the news to News4Jax: “They sat us down on the couch, and they told us they found her.” She added, “The first thing Steve said was, ‘Where was she?’ Police said, ‘Right across the street.'”
Jessie described the morning her family got the news: “I came downstairs, and my family was standing in a circle, and it was just like any other day.”
The Confession and Pornography Bombshell
Investigators pulled Joshua Phillips out of school immediately and took him to the police station for interrogation. His father, Steve, was present during the questioning and told his son to tell the truth.
Joshua confessed to the killing at the station, saying it happened by accident and he panicked.
His mother and other family members struggled for long afterward to reconcile the boy they knew with what he had done. Melisa told CBS News, “That’s not the way he is; he’s never hurt anybody.”
However, their claims and his confession unraveled almost immediately after the police focused their investigation on the boy. Investigators found no blood in the backyard to back up the claim of accidentally hitting Maddie. There were no blood or fibers on the baseball bat either.
Instead, his computer revealed a cache of violent pornography. Computer forensics teams checked his hard drive and showed that he had been actively viewing these files right up to the time frame he encountered and killed Maddie. He had also opened these files after murdering her.
This prompted the investigators to consider the possibility Maddie was also sexually assaulted before her murder.
Crowds gathered in the streets in complete disbelief. The focus had just shifted from a rescue operation to a criminal prosecution, and state attorney Harry Shorstein announced the intent of the state to try Joshua as an adult for first-degree murder.
An autopsy was done, and in January 1999, Medical examiner Dr. Bonifacio Floro concluded that the official cause of death was multiple blunt impacts to the head. Combined with several stab wounds. There was no indication of sexual assault.
Four days after his arrest, Maddie was buried.
The Trial of Joshua Phillips
The trial officially began on July 6, 1999, and Phillips was tried as an adult. Because of his age, however, the death penalty was legally off the table, making life in prison the maximum possible penalty.
The trial was also relocated from Jacksonville to Bartow, in Polk County, to ensure an impartial jury.
The prosecution laid out a damning case, using the physical evidence at the scene, the recorded confession, and the brutal nature of Maddie’s injuries. The defense succesfully restrained the prosecution from presenting evidence of pornographical material on his computer because they maintained it would cause prejudice against their client.
The prosecution did however, maintain that the crime was sexually motivated, because Jessie testified that Phillips had a history of talking about inappropriate sexual matters with both her and Maddie.
In an unusual tactical move, the defense team also called no witnesses and presented no evidence. They only relied on a closing argument centered on Phillip’s age and his fear of an abusive father to explain his behavior.
Steve and Melissa had also hoped for a lesser charge like second-degree murder or manslaughter that could have allowed for their son to be released earlier. They also hired psychologist Tom Bowery to evaluate him.
Phillips told Bowery he was not anxious or depressed, and he loved his parents. According to CBS News, Bowery said, “This is not what I would’ve seen as the typical kind of sociopathic, wanting to kill, wanting to maim, deriving-pleasure-from-the-pain-of-others kind of kid. I don’t think that’s true at all.”
On August 20, 1999, circuit judge Charles Arnold sentenced Phillips to life in prison without the possibility of parole. CBS News reported his statement saying, “I do not perceive you to be a child. Your monstrous act made you an adult.”
Phillips stood with his head bowed and showed no emotion. His father Steve called the prosecution ludicrous and obscene. Sheila Clifton thereafter addressed the court and described an effervescent little girl. “No one or nothing can look up at me with those big brown eyes. Pictures and memories, that’s all I’ve got.”
For the next 19 years, Phillips served his sentence at the Marion Correction Institution in Lowell, Florida.
A Second Look
In 2012, the US Supreme Court ruled that mandatory life sentences without parole for juveniles were unconstitutional. This decision was also applied retroactively, and in 2017, Phillips returned to court for a resentencing hearing.
His attorneys argued that Phillips had since been rehabilitated, but the Clifton family said he should never be released. Now remarried, Sheila DeLongis, Steve Clifton, and Jessie all testified at the trial.
Action News Jax reported Sheila’s irritated rebuttal, saying, “I’ve sat here in this courtroom and listened to all of the classes that the defendant has been able to take. What classes had Maddie been able to take over the past 18 years?”
She added, “Should he be released from prison, I pray I will no longer be on this earth.”
According to News 4 Jax, Phillips took the stand and addressed the Cliftons, saying, “I did something horrible. I am so sorry, so sorry for what happened. I wish to God that I could have known this or understood this when I was 14. Had I then, none of this would have come about.” He continued: “I don’t pretend to know or understand your pain or to grasp the void I created in your lives.”
Jessie said the apology arrived as a shock. She told Action News Jax, “It was good to hear. It still doesn’t change anything, but I think it needed to be said.“
She also added, “Every time the word forgiveness is brought up, all I see is that guy on the stand showing how he did it, and it’s just like, how do you expect me to take on that burden to forgive you? I can’t.“
Since the legal scope had changed, prosecution was now allowed to focus on the pornography aspect in the case. They revealed that before the murder Phillips had turned on his computer to watch violent pornography.
The state then used the timeline to show Phillips was in a state of sexual arousal and his actions were premeditated rather than panicked. By focusing on the fact Phillips hid the body under his bed and went on watching pornography, the state argued his actions showed an extreme level of depravity.
Hence, the prosecution convinced circuit court judge Waddell Wallace the crime was heinous.
‘Life in Prison’ Again
Judge Wallace resentenced Phillips to life in prison but with the possibility of review, twenty-five years after the initial sentence. Standing beside her mother after the hearing, Jessie told First Coast News, “No one should ever have to go through this twice; we did it.”
In June, DeLongis issued a statement rejecting suggestions that her daughter’s killer deserved leniency.
News 4 Jax reported her statement, saying, “Maddie didn’t get a second chance. She didn’t get to grow up, graduate, fall in love, or have a family of her own. Maddie’s sentence was final. Her killer’s should be, too.“
Jessie Clifton said she also intended to testify again and read a new victim statement saying, “I want him to see how bad I’m hurting and that I don’t really care that he’s hurting or wants to get out of jail.”
Bernie de la Rionda, the prosecutor who handled the resentencing in 2017, called the case one that permanently marked the community.
In March 2026, Phillips withdrew his bid for sentence review, citing a need for professional counseling before proceeding. He told News 4 Jax, “As always, I wish to convey my deepest apologies to Maddie’s family for the reopening of wounds that any legal action in my case surely causes.“
Maddie’s family continues to mark the anniversary of her death every November. On one of the anniversaries, Delongis said the family was holding strong, and Maddie remains with them.
Her case shows the tragic potential of danger to children posed by even the most harmless-looking individuals around them. Her story bears similarities to Leigh Occhi, who disappeared from her home after being left alone for an hour.
The difference is Maddie’s body was found after a week, but the same likelihood exists that someone close to Leigh was likely behind her abduction and probable murder.
For more true crime stories involving murders, check out our articles on Frauke Liebs and Jane Longhurst.
