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Murder in New Bedford: The Unsolved Case of New England's Deadliest Serial Killer

Nine women turned up dead. Two more were never found. To this day, the killer remains at large.

new bedford highway killer

It’s been 29 years since a murderous rampage swept through the town of New Bedford, Massachusetts. On July 2, 1988, the remains of Deborah Medeiros—a 30-year-old prostitute—were found along Route 140 just outside of New Bedford. Soon thereafter, additional women disappeared from the streets of New Bedford, with their remains eventually turning up in the area.   

By the end of the killing spree, investigators had discovered nine bodies. The remains of Christine Monteiro and Marilyn Roberts were never found, though it is believed that they too were victims of the same killer. Both women are now presumed dead. 

While multiple suspects were considered, the case remains unsolved to this day. Pulitzer Prize finalist Carlton Smith argues in his book Killing Season that authorities were closing in on the killer—but that police officers and politicians could not put aside their personal agendas in time to capture the madman. 

Read on for an excerpt from Killing Season: The Unsolved Case of New England's Deadliest Serial Killer, and then download the book. 




Killing Season

By Carlton Smith


Nancy Paiva’s descent into the hell of heroin came to an end sometime that same evening.

The exact circumstances of Nancy’s disappearance remain obscure. What is known is that sometime during the afternoon, Nancy was sitting in a south end New Bedford bar called Whispers, along with Frankie Pina, and several other people.

According to some of those present, an argument between Nancy and Frankie ensued, with Frankie ordering Nancy to leave the bar. Nancy left. An acquaintance later told Judy DeSantos that she saw Nancy walking up the street toward her house around 7 P.M., with tears in her eyes. It was raining. That was the last time anyone saw Nancy Paiva alive.

The Whispers Pub was a notorious hangout in New Bedford’s south end. Later, it would be alleged in federal court that the establishment was the center of a cocaine ring that handled sales of nearly $5.2 million each year.

Almost all of these sales went to New Bedford residents—including, it would later be learned—to many of the victims of the Highway Killer. Cocaine was so easy to procure in the bar that a line of would-be buyers often formed, heading down the stairs to the basement to wait their turn to purchase the drug. It was just after leaving Whispers that Nancy was last seen.

Two days later, after the afternoon Nancy left Whispers, Sergeant John Dextradeur of the New Bedford Police Department was on his way back to the detectives’ squad room, when he saw something that disturbed him. Dextradeur dropped what he was doing and walked over to the front desk to eavesdrop.

The man at the counter was Frankie Pina, and Dextradeur knew him well. In fact Dextradeur had once arrested Frankie for armed robbery, and those charges were still pending.

Now Frankie wanted to file a complaint with the police, and Dextradeur was really bothered.

“I don’t know why,” he said later. “I just felt that it was out of character for Mr. Pina to be casually standing at the front desk of the police lobby speaking to an officer. Usually when Mr. Pina was at the desk in the lobby, he was there in handcuffs, against his wishes.”

Learning that Frankie was reporting “Nancy Pina” as a missing person made Dextradeur feel even more uncomfortable.

The last time the detective had seen Frankie—in April 1988—Frankie had been with another woman, who appeared to have gone missing as well. Twenty-six-year-old Rochelle Clifford had been with Frankie on April 27, 1988, but had seemingly vanished shortly thereafter.

new bedford highway killer
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  • Victim Nancy Paiva

    Photo Credit: Open Road Media

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That earlier disappearance was irritating to Dextradeur, because Rochelle Clifford was a key witness in two open cases Detective Dextradeur had in his files, one a rape, and the other an assault; if Dextradeur could only find Clifford, he might be able to resolve those two cases and get busy on something else. But for two months Rochelle Clifford had been nowhere to be found, and here again was Frankie Pina, now talking about a second woman connected to him, who was also missing—the woman he lived with, in fact. To Dextradeur, that seemed to make Frankie two for two. It was enough to make a detective think.

Even as Frankie was known to the cops in New Bedford, so was Nancy Paiva—actually, of course, as “Nancy Pina,” although Nancy and Frankie had never been married. The way the police knew Nancy was as Frankie’s regular victim: countless times police had been called to “Nancy Pina’s” Morgan Street apartment to keep Frankie from beating Nancy, or at least rescue her after he’d already started.

Now, with Frankie reporting the woman he beat so often as newly missing, as well as Frankie’s earlier connection to Rochelle Clifford, Dextradeur was immediately suspicious of Frankie. Dextradeur wanted to know more, so he told Frankie he would personally investigate Nancy’s disappearance, even though handling missing persons cases was not his job. Actually, what Dextradeur had in mind was investigating Frankie.

Dextradeur and Frankie moved out to the front steps of the police station, and talked for more than an hour about Nancy, Rochelle Clifford, and Frankie’s most recent criminal activities. Frankie, in fact, was about to go to jail again on yet another assault charge.

As Dextradeur put it later, “I just felt uncomfortable with the whole thing … It was really strange. It was just that I was sitting there talking to a guy that I can’t gather any respect for, knowing his background. And he’s showing me this great love and concern for this girl that he used to beat the hell out of so regularly.”

Why was Frankie suddenly worrying about Nancy? Had Frankie done something to Nancy, and was he now trying to cover it up by acting worried? Had he likewise done something to Rochelle Clifford? Dextradeur assured Frankie that he would give Nancy’s disappearance an all-out effort.

The next day, Judy DeSantos learned of Nancy’s disappearance for the first time. She found out from Nancy’s daughter Jill, who heard from Jolene. “Jolene says Mom hasn’t been home for three days,” Jill told Judy. “Do you know where she is?”

It wasn’t unusual for Nancy to stay away from Frankie, Judy knew, but almost always before, she had gone to stay with Judy, or sometimes with friends. Judy called around to see if anyone had seen Nancy, but no one had. She waited for two more days, thinking Nancy might turn up, but Nancy didn’t. By this time Judy was really worried about her sister.

She thought about calling the police, but was intimidated by the idea of talking to the authorities. She thought the police might think she was being hysterical. But through a friend, Judy learned the name of a detective in the department. Judy called and reported that her sister, Nancy Paiva, was missing. Judy also told the police that her sister was addicted to heroin. That was a mistake, Judy decided later, because then the detective told her that Judy just had to understand that “junkies disappear all the time.”

Judy knew that wasn’t true about Nancy, however. No matter how badly addicted Nancy was, she always made an effort to maintain contact with her children, or with Judy herself. It just wasn’t in Nancy’s nature to disappear without leaving word with someone. But because Judy was intimidated by the confident attitude of the police, and secretly ashamed of Nancy’s addiction, she at first meekly accepted the department’s cavalier verdict about her sister. She sat down by the telephone and waited for Nancy to call.

Want to keep reading? Download Killing Season: The Unsolved Case of New England's Deadliest Serial Killer now. 

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Featured image of victims (left to right) Marilyn Cardozo Roberts, Dawn Mendes, and Deborah Greenlaw Perry DeMello: Open Road Media