How “Preppy Rapist” Alex Kelly Eluded An 8-Year Global Manhunt

Alex Kelly mug shot [Darien Police Department]

In 1986, the same year that Robert Chambers shocked New York City as “the Preppie Killer,” 18-year-old Alex Kelly scandalized the nearby upscale suburb of Darien, Connecticut, as “the Preppy Rapist.”

Related: 30 Years Later: How “The Preppie Murder” Reinvented Feminism

Kelly grew up in the elite, the son of Joe Kelly, a self-made plumbing mogul, and Melanie Kelly who came from old money and worked as travel agent.

Alex graduated from Darien High School in 1986. He radiated popularity as a sports star on campus and a well-regarded presence in the community. Yet that veneer concealed troubling facts.

Alex Kelly mugshot, Darien Police Department

Alex Kelly mug shot [Darien Police Department]

At 15, Alex led friends on a nine-month crime spree. They burglarized neighborhood homes, stealing money and silverware to peddle in Manhattan for drug money.

After getting busted, Joe and Melanie repaid the robbery victims $100,000 and hired a legal team that pleaded Alex down from a nearly three-year sentence to two months in a juvenile rehab.

The pattern, then, was set: Alex would break the law, and his parents would pay up to bail him out.

Related: “The Preppie Murder” Was 30 Years Ago, But Is Still Leaving Its Mark On Pop Culture

On February 10, 1986, Alex Kelly, in his senior year, offered a ride to Adrienne Bak, a 16-year-old Darien High sophomore. He pulled the car over, physically attacked Adrienne, and forced her into the backseat, where he raped her.

Upon dropping her off at home, Kelly warned that if Bak said anything, he’d do it again, only he’d kill her next time. Bak went to the police the next morning.

Three days later, Kelly raped and sodomized 17-year-old Hillary Tollet just a few miles away in Stamford, Connecticut.

Alex Kelly, Darien High Yearbook

Alex Kelly [Darien High Yearbook]

Authorities arrested Kelly and put him through the system. The charges scandalized Darien.

While out on bail, Kelly’s presence reportedly sparked such animosity among local defenders and detractors that a judge allowed him to relocate to Colorado, near his parents’ Aspen condo, for the year or so until his scheduled trial. The only condition was that he had to return to court. That’s what Alex Kelly did not do.

What should have been the beginning of jury selection in the Alex Kelly rape trial on February 17, 1987 turned into the revelation of a new crime. The defendant was nowhere to be found. Kelly had already quit his job and vacated his residence in Colorado. His parents claimed to have no idea where he could possibly be.

Three days before the trial start date, Alex Kelly fled to Europe where, for the next seven years, he bounced between 15 different countries, traveling in first-class luxury all the way.

Related: Preppies, Yuppies, And The Deadliest Decade: How Key ’80s Terms Connect To Killer ’80s Crimes

Fully funded and feeling no fear, Kelly preferred the winter resorts of Sweden and Switzerland, living it up as a pampered playboy and international jet-setting “ski bum.”

Throughout it all, Kelly repeatedly eluded authorities. The FBI tracked him to an island off the cost of Sweden. Interpol raided the house where Kelly had been living with a new girlfriend. They missed him. Time and again, all over the planet, they missed him.

The case finally broke in 1994. Newly assigned FBI agent Ralph DiFonzo reasoned that Alex’s well-to-do parents simply had to be footing the bill for his fugitive existence. He then focused the investigation on establishing that link.

The following year, agents searched the Kellys’ home and discovered not only financial records tying Joe and Melanie to their son’s life overseas, but photographs of the family members reunited in Europe on at least one ski vacation.

The feds cut off Alex Kelly’s money line and, in January 1995, the fugitive “Preppy Rapist” surrendered to authorities in Zurich and flew back to Connecticut in chains. He would be tried separately for the rapes of Adrienne Bak and Hillary Tollet, with each jury hearing nothing about the other case.

Alex Kelly maintained that sex with both girls had been consensual and that they were, in fact, simply lying.

During the first trial in October 1996, Thomas Puccio, Kelly’s attorney, aggressively challenged Adrienne Bak’s claim that Alex kept his hand on her throat throughout the incident. Puccio focused on how that would have made it impossible for Kelly to put the backseat of his car into a reclining position, as that would require both his hands.

After three days of deliberation, the jury said it could not reach a verdict, and the judge declared a mistrial. The case returned to court in April 1997. This time, the jury quickly convicted Kelly and he got 20 years, the maximum sentence.

Shortly thereafter, Kelly pleaded no contest to the rape of Hillary Tollet. He received a 10-year sentence to be served concurrently with his previous conviction.

In all, Alex Kelly spent ten years behind bars. He received parole in 2007 and presently lives in Connecticut, where he works as a skydiving instructor.

Adrienne Bak Ortolano has become an outspoken advocate for victims of sexual assault. Hillary Tollet married and moved away from Connecticut, and she chooses not to address the case in public.

While Alex Kelly enjoyed an eight-year vacation on the lam, four more girls came forward to assert that he had raped them. Two of the alleged victims were 13 years old.

Learn more about the case in the Investigation Discovery series Vanity Fair Confidential. Watch new episodes on ID GO and Mondays at 9/8c. 

Read more:
New York Times
Darien Times
Entertainment Weekly
Yale Courant
Daily Mail

Main photos: Alex Kelly mug shot [Darien Police Department]



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