Ana Maria Angel: The Abduction and Murder of a Miami Local

In a city where daily stories of brutal murder are generally read with the same passing apathy as a West Coast box score, it becomes hard to find a crime that will shock anybody in South Florida. But that is exactly what happened in the spring of 2002, when two South Miami high school seniors went out for a date, and one of them never came back. This horrific tragedy saddened even the hardest of Miami hearts when honor student and soccer captain Ana Maria Angel was found shot to death on the side of Interstate 95 near Boca Raton, having been brutally gang-raped and her boyfriend assaulted to within an inch of his life. The first of the five men charged with this crime was sentenced to death this past summer, and to many it seemed an appropriate punishment for perhaps the most brutal and vicious act of random violence in Miami history.

Horror In South Pointe Park

On the night of April 27, 2002, Angel and her boyfriend Nelson Portobanco went out to celebrate their five-month anniversary with dinner at Los Ranchos in Bayside. After the meal, the couple decided to go for a romantic moonlit stroll near South Pointe Park in South Beach. As the walk ended, the couple attempted to return to their car when they were ambushed by five men, one wielding a gun and another a knife. They forced the couple into a pickup truck, and dragged them off for a night of incomprehensible terror.

According to testimony from Portobanco and the accused criminals, the men, concerned about security guards who regularly patrolled the area, forced the couple to the floor of the rented Ford F-150. They told Portobanco to put his head between his knees, then demanded Angel’s ATM card and PIN. Upon receiving both without objection, the assailants stopped at an Amoco station on the 3600 block of Biscayne Boulevard and withdrew some money, stopping at another gas station before heading north on I-95.

Once on the highway, several of the men made their way to the back of the extended-cab where Angel was being held. Portobanco was repeatedly assaulted and forced to keep his head down while the attackers held his girlfriend. As she cried and begged them not to, the assailants took turns raping her as the truck sped up the highway. They brutalized the young woman for almost 20 minutes, which must have seemed like an eternity to Portobanco as he heard, but could not see, what was happening to Angel.

As the truck reached north Broward County, the men forced Portobanco from the truck and, behind some shrubs that shielded them from on-looking cars, beat and stabbed him over ten times. The teenager decided to play dead in hopes of the attack stopping before he was killed. After slitting his throat, the assailants kicked Portobanco a few more times, then stomped his head to the ground for good measure before taking off in the truck. Portobanco, thinking that Angel had also been thrown out of the vehicle, searched for her briefly before running to the shoulder of the interstate to find help. A passing motorist assisted him and took him to the hospital, where he reported the crime.

As the attackers realized their rental truck was due back in Orlando the next day, they quickly decided to rid themselves of their last victim, Ana Maria Angel. When they were finished raping her, they pulled over just before the Palmetto Park Road exit in Boca Raton, dragged her to a retaining wall, and as she begged for her life shot her once in the head at point blank range. For the first few days after the crime, the Florida Department of Law Enforcement and local authorities conducted a massive manhunt for Angel, as Portobanco and her family hoped she would be found alive. Family members even left voicemail messages on her cell phone begging the kidnappers not to harm her. But a few days later Angel’s body was found right where the killers had left it, her hands frozen in a praying position, as if she had died begging for her life.

Bad Guys Get Caught Quick

It did not take long for Miami Beach police and FDLE officials to track down the killers. Going off a traced cell phone call and some anonymous tips, the combined authorities arrested five men in Orlando. By April 30, FDLE officials had arrested brothers Victor Manuel Caraballo and Hector Manuel Caraballo, Joel Lebron, Cesar Mena and 16 year-old Jesus Roman for the murder, assault, robbery and rape of the couple.

Lebron, who broke down in tears during his confession, admitted to being the shooter. Intent on killing the young woman, Lebron admitted that the first two times he had tried to shoot Angel his weapon had not fired because no bullet was in the chamber. Only after his third attempt, and listening to the young woman beg for her life as his revolver would not fire, was he able to complete his crime. His confession also led police to Angel’s body, saddening investigators but giving them enough evidence to move forward with the case. The suspects were all brought to Miami-Dade County and held under suicide watch. All had threatened to kill themselves upon arrest.

Nobody Likes A Sadistic Kid Killer

After being transported to Dade County’s Metro West Detention Center, Lebron was quick to take advantage of what he perceived as his celebrity-criminal status. What he did not understand, however, is that this criminals’ reverence is held for perpetrators of spectacular crimes, not cowardly acts of disgusting violence. Especially ones for which you are caught in less time than it took to commit the crime. So while Lebron bragged incessantly upon his initial incarceration about the evening of April 27, his fellow inmates were, appropriately, disgusted. Even hardened criminals, apparently, find it offensive when you brag about raping and killing an innocent girl. And so within a few weeks of arriving at Metro West, Lebron was transferred into protective custody after it was discovered that inmates were planning to kill him long before he would ever stand trial for the brutal crime.

While in protective custody at the pretrial detention center, Lebron then tried to arrange a hit on both a family friend who he believed turned him in, and on Portobanco so that no eye witness could testify against him. Lebron, apparently, was not familiar with DNA evidence often gathered at rape scenes. When word of his attempts reached the police, they sent an undercover detective in to meet with Lebron to arrange the hit. His offering price: $250. Lebron was never charged with anything as a result, but it was troubling for those on the outside who still fear the man who has long since been put behind bars.

A Botched Confession

While everyone in South Florida, from its most upstanding of citizens to the dregs of its jails, was disgusted with the South Pointe 5, fortune would prove to be their only friend. Lebron’s confession, considered a key piece of evidence in not only his prosecution, but in that of the other four defendants, was apparently non-existent. That is not to say that it never happened, but when Miami Beach Police Detective Larry Marrero sent tapes of the confession to FDLE agent Ed Royal, who had also been an important part of the investigation, he found them to be completely blank. Assuming Marrero had sent him the wrong tapes, Royal asked for the detective to send another copy. When he went to copy the originals, Marrero discovered that those too were blank.

Apparently, the device used to record the confession had two settings, one to record telephone conversations and the other to record live ones. Marrero had not switched the setting over from his previous use of the device, and therefore recorded 90 minutes of dead air, leaving no audible proof of what Lebron had told him.

One would think investigators would be crushed by such a blow, but thanks to DNA evidence and witness testimony, prosecutors were able to continue with the case. It wouldn’t have mattered anyway: Judge William Thomas threw out the confession as he ruled the suspect had not been properly advised of his Miranda rights.

The First To Get Put Away

While the dismissal of a confession and the lack of a good eyewitness (Portobanco later admitted he could not positively identify at least one of the defendants) may have seemed an ominous sign for those seeking justice for Ana Maria Angel, DNA evidence and testimony from the defendants themselves has proven enough to convict at least one of the killers thus far. As each member of the South Pointe 5 has claimed to have done nothing but watch the others commit the crime, prosecutors have applied the felony statute to the case, holding anyone associated with the committing of a crime as responsible as the one who actually did it.

The first to stand trial was Victor Caraballo, who claimed not only to have not beaten or killed anyone, but not to have raped Angel either. He says he feared he would catch AIDS if he had done so. His brother Hector, who was infected with the disease, had already raped her repeatedly. He claimed the DNA evidence found on Angel’s body was from his masturbating on her, and as such he was not guilty of the rape. The jury saw it differently.

This past April, nearly five years after the horrific crime, Caraballo was found guilty of first-degree murder, attempted murder, armed sexual battery and two counts of armed kidnapping and armed robbery. The jury recommended the death penalty, and Judge Thomas agreed. Caraballo had requested the death penalty. He faced life in prison without the possibility of parole and, claiming mental illness, said he did not want to spend the rest of his life in prison. As it stands, that is exactly what he will do, but his life will be, at least presumably, considerably shorter.

A Hopeful Precedent For Survivors

It is not certain if similar fates await the other four men involved in the crime. Caraballo was the first to stand trial, but this means that in order to see justice carried out Portobanco and Angel’s family will have to endure reliving that horrific night four more times. If Caraballo’s case is used as a precedent, it is not unlikely that three others will also receive the state’s ultimate penalty. Roman, who was 16 at the time of the killing, cannot be sentenced to death since he was a juvenile.

Angel’s mother, Margarita Osario, who had moved to Miami from Medellin, Colombia for more safety and better education for her only child, is currently suing Penrod’s for lack of adequate security. A similar case, filed against the City of Miami Beach, has been dropped. The system will deal with the criminals but she, and her co-plaintiff Portobanco, seek the financial damages for the pain and suffering they have endured. Penrod’s, which owns much of the property around where the assault began, has not commented on the issue due to pending litigation.

The reason this particular crime shook crime-ridden South Florida so much is simple: When one reads about drug dealers killing one another, or rival gang members in a bad neighborhood shooting each other up, or even tourists getting shot by vicious street criminals, locals believe it still won’t happen to them. I’m not a drug dealer, I’m not in a gang, I’m not a tourist stupid enough to get off the 112 before I reach the airport. But when it is an innocent Miamian out doing what millions of us have done week in and week out, it scares you. It makes you realize that as safe as you usually are, you never know who is lurking behind the bushes. Even in what is generally considered a rather safe area south of Fifth.

So while many in Miami will watch the next four trials rooting for justice for Ana Maria and her family, we are also rooting for ourselves. For the next time anyone takes a moonlit stroll on the beach, they may not be fearful, but they will no longer feel as comfortable as they might have before April 27, 2002. And that loss, while minuscule compared to that of Osario and Portobanco, is enough to make everyone in South Florida hungry for justice.

The Five Monsters Who Kidnapped, Raped, and Killed Ana Maria Angel

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Editor's Note: Originally published on November 13, 2007 and updated in 2026 for clarity, while preserving Matt Meltzer’s storytelling and investigative detail.