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Story By John Murray

John Regan is so dangerous that even after serving a 12-year prison sentence for kidnapping, the state of New York has kept him confined in civil management for the past four years arguing he is not rehabilitated, and is a potential menace to society.

After 16 years of incarceration, Regan, 64, wants his freedom. If he wins a decision in a closed mental health trial in Plattsburg, New York, he could be a free man.

John Regan was arrested in Saratoga Springs in 2005 on kidnapping charges.

Regan committed one of Waterbury’s most publicized crimes of the past three decades when in 1993 he climbed onto a roof, put on a hood and a bad Jamaican accent, entered a second story window and raped his good friend’s wife. It took 11 years to solve the crime, and even then, many in Waterbury refused to believe that Regan, hailing from a prominent family in the city, could have been so evil as to press a gun against Donna Palomba’s head and rape her while her two little children slept down the hallway. It was the first night her husband, John, had been away from home in 11 years of marriage.

Donna Palomba

Two detectives in the Waterbury Police Department had questioned her story from the beginning. A snitch had given a tip to the detectives that Palomba was having an affair when one of her children unexpectedly walked into the bedroom and she’d made up the sexual assault story as an alibi. It was bad information from a snitch that led detectives to threaten Palomba with arrest and the loss of her kids if she didn’t confess to lying. It was a second major confrontation in a month for Donna Palomba, and psychologists later described the encounter with the police as even more harmful to her mental health than the rape.

Palomba fought back and sued the Waterbury Police Department, and in 2001 she won a $200,000 judgement in Jane Doe versus the City of Waterbury. Two key witnesses testifying in her favor at the trial were world renowned forensic scientist Dr. Henry Lee, and Waterbury detective Neil O’Leary, who is now the Mayor of Waterbury.

Even after Palomba won the trial, the Republican-American newspaper published an article that left the public questioning “Jane Doe’s” credibility, and those who knew that Jane Doe was Donna Palomba, were left with lingering doubts about her story.

The Waterbury Observer published an 11-page report in April 2001 that detailed Palomba’s nightmarish experience with a rapist, the Waterbury Police Department and the Republican-American newspaper. At the time of publication Palomba had still not revealed her identity to the public, and the Observer referred to her as Rachel in its reporting.

Donna Palomba tried to set the record straight by sharing her story with the Observer.

The Observer’s story helped Donna Palomba’s healing process from PTSD.

Three years later a DNA match revealed that John Regan was the rapist, and he was arrested. Regan pleaded not guilty at his arraignment and was set free on a $350,000 bond. Many in the community saw Regan as a stable father and husband and refused to believe he was a rapist. Infidelity and an affair with Donna Palomba, yes, a sexual predator, no.

One year later his charade exploded when Regan was arrested on Halloween for trying to abduct a 17-year-old track star in Saratoga Springs, New York. Police found duct tape, a tarp, rope, photography equipment and a shovel in the back of his van. Regan’s mask was yanked off on Halloween revealing a monster. Overnight, stacks of cold case files in the New York, Massachusetts and Connecticut were re-opened. The respected family man was now a suspect in a series of unsolved homicides.

Was John Regan the serial killer who murdered four Waterbury prostitutes in the 1980s and 1990s and left their naked bodies along the Naugatuck River in Harwinton? Where was John Regan when Molly Bish vanished in Massachusetts? Where was John Regan when a college student disappeared in Albany?

Law enforcement was unable to link Regan to any of the murders and disappearances, but other women have stepped forward to accuse him of other sexual assaults.

Regan’s attack against Donna Palomba, and his bold kidnapping attempt in Saratoga Springs, triggered a two-hour NBC Dateline special in 2007 titled, “The Man Behind The Mask.”

Regan was eventually tried and convicted in New York for kidnapping and given a 12-year sentence. When his time was up, authorities in New York applied the Sex Offender Management and Treatment Act which targets sex offenders who have a mental abnormality that predisposes them to commit sex offenses, and who have serious difficulty in controlling their conduct.

Nineteen states have laws that permit civil management of certain sex offenders after they have completed their prison sentence. Regan was placed on trial in 2017 and was confined in a psychiatric facility run by the state Office of Mental Health.

Regan could be set free by a judge, or returned to psychiatric facility in New York.

Regan is again seeking his freedom and is currently standing trial a second time. The proceedings are closed, but The Waterbury Observer has confirmed that victims have testified during the mental health proceedings in Plattsburg, New York.

“There was compelling evidence that he is a serial rapist,” Mayor Neil O’Leary, the former Waterbury detective credited with solving the Palomba case, said in the past. “John Regan could be a continued threat to society, but if he wins, he’s out.”

O’Leary declined to provide details about his recent testimony in New York citing privacy concerns surrounding mental health issues.

Waterbury Mayor Neil O’Leary.

And if Regan is successful in his attempt to gain freedom and comes back to Waterbury?

“If he comes back to Waterbury we won’t violate his rights,” O’Leary had said, “but we’ll know where he lives, and will keep an eye on him.”

NBC Dateline has continued to follow the case, and after the verdict the program will air another two-hour special report. Production crews were in Waterbury in 2020 and 2021 re-interviewing subjects as they retold the story, this time filming in high definition.

This time around the special will include more details about the non-profit organization Donna Palomba organized in 2006 – Jane Doe No More, after she stepped out of the shadows and hurled her Jane Doe name tag to the curb. The organization empowers survivors of sexual crimes to find their voice, advance their healing and educate others. Part of the Jane Doe No More mission is to help create a society that no longer spreads doubt, instills fear, casts shame or places blame on survivors of sexual crimes.

(For more information about Jane Doe No More check out https://www.janedoenomore.org)