The Murder of Concetta “Penney” Serra Part 1 (Connecticut)

It was July 16, 1973 and 21-year old Concetta “Penney” Serra had the day off from her job as a dental assistant at a practice in downtown New Haven, Connecticut. She argued with her little sister over who would get the keys to the family’s Buick that day, and won, driving away from the home she shared with her father and sibling late that summer morning.

Penney made it into the Temple Street Parking garage adjacent to Malley’s department store just before 12:45 p.m. She told her father earlier that day she planned to do some furniture shopping. But before she ever stepped foot outside of the garage, Penney came face to face with evil in a senseless attack that claimed her young, promising life.

Despite the abundant evidence left at the scene by the perpetrator and considerable public speculation concerning one suspect in particular, more than a decade would pass before New Haven Police were able to make an arrest. But was their case against the man they identified as Penney Serra’s killer built on solid ground? One critical detail would derail everything, and the investigation started all over again.

When Penney Serra’s murder finally made it to trial 29 years later, the judge would call it, “one of the most mysterious murder cases in New Haven’s history.” The mystery would reach a conclusion, but not without a figurative rollercoaster of false arrests, cover-up allegations, elaborate reenactments, and eventual advancements in forensic science to finally put the case of Penney Serra to rest.

This is Part 1 of 2 in Penney Serra’s story. Follow Dark Downeast wherever you get your podcasts to hear Part 2 as soon as it drops on July 24, 2023.

About Concetta “Penney” Serra

Concetta “Penney” Serra was born in New Haven, Connecticut on March 2, 1952 to her Italian American parents John and Pauline Serra.

John Serra spoke warmly about his daughter, telling Helen Bennett Harvey of the New Haven Register, “All the people who knew Penney loved her, she was beautiful, she was funny. All of her girlfriends loved her. She was fantastic.”

Penney grew up fast, and assumed the homemaker and mothering role for her family when her mom Pauline passed away in 1963. She was only 11-years old at the time, but Penney took care of her little sister, Rosemary, and even cooked dinner for her father so he’d have a warm meal to eat after a long day working at his auto repair shop.

I learned a lot about Penney and her life from a book by Henry C. Lee, one of the world’s most renowned forensic scientists who worked on such infamous cases as JonBenet Ramsey, Laci Peterson, and Helle Crafts. Lee also worked on Penney Serra’s case. In his book, Cracking More Case: The Forensic Science of Solving Crimes, Lee examines Penney’s case alongside four other homicides through the lens of advancements in forensic technology that finally revealed long-sought answers.

Henry C. Lee became the director of the Connecticut State Police Forensic Science Laboratory in 1979, four years after the initial investigation into Penney Serra’s murder began. However, he held the position for over 25 years and played a role in the renewed investigation in the late 80s and early 90s. He has first-hand knowledge of the intimate behind the scenes details of the investigation. I’ll link his book in the description of this episode for you – it’s available in free digital format via archive.org.

Henry Lee wrote that Penney, along with taking care of her sister and managing the Serra household in her mother’s place, also learned to manage her father’s business and assisted with his bookkeeping. She was smart, sharp, and wise beyond her years – it’s what the circumstances of her life demanded.

But she was still a kid, too. At Wilbur Cross High School, Penney sat on the prom committee for her junior and senior year. In the 1971 yearbook, she listed her future plans simply as “college”, but those plans were delayed, at least temporarily, in favor of earning some money. In 1973, 21-year old Penney worked as a dental assistant at an office on Chapel Street in New Haven.

For a time, Penney was engaged to a man named Philip DeLieto. Phil worked at his family’s luncheonette about a mile away from the dental office where Penney worked. According to Henry Lee’s book, Philip was distantly related to the New Haven police chief at the time, Biagio “Ben” DiLieto (but spelled Di instead of De, like Phil’s last name). That familial connection would later be a point of contention in a long-lasting investigation.

Despite their engagement, Phil and Penney’s relationship was plagued by arguments and disagreements. Penney was the one to call off their engagement, but the former couple stayed close. They still made plans and spent time together and even traveled as friends, right up until the day Penney was killed.

July 16, 1973

It was July 16, 1973, and Penney had taken the day off. Though some 21-year olds might use a free hot and humid summer day to hit the beach or hang out with friends, Penney wanted to run some errands, pay some bills and maybe stop by Phil’s family’s restaurant to say hi.

She’d need to borrow her dad’s car to get around that day, but her sister Rosemary tried to call dibs on the 1971 two-door blue Buick Electra 225. Penney had seniority though, so little sis surrendered the keys and Penney left the house by 11 a.m. that morning.

Her first stop that day was her father’s auto shop where she got caught up on the bookkeeping and visited for a few minutes before carrying on with her to-do list. Penney told her dad she planned to do some furniture shopping at Edward Malley’s department store, and left the shop by 11:30 a.m.

Where she went and who she saw during the next 75 minutes is still unknown, but by 12:42 p.m. Penney had pulled into the Temple Street parking garage through the Frontage Road entrance and parked her car on the ninth floor. By 1 p.m. Penney Serra was dead. She never made it out of the parking garage alive.

Investigation

A parking garage attendant making his rounds on that July afternoon found her lying at the base of a corner stairwell on the 10th floor of the parking structure. Her shoes were gone, and the soles of her feet were blackened as if she’d been walking, or running, barefoot. Her blue dress was blood soaked, and it was clear to the attendant that the woman was dead. He quickly made for the phone to call the police.

As he waited for the sirens to climb the several levels up to where the woman lay, the attendant descended from the 10th to the 9th floor, where he found what he believed was a brown wig. It was among the first pieces of evidence collected and tagged in the case.

Lee detailed the extensive evidence collected from the parking garage and from the Serra family Buick itself. The car Penney borrowed from her father that morning was parked at a strange angle on the 8th level of the garage and the driver side front door handle had what appeared to be blood on it. Inside the car, crime scene technicians found a pair of women’s shoes and a purse with a wallet containing about $15 dollars as well as a Connecticut driver’s license belonging to Concetta Serra.

The backseat of the car had more blood-like stains on the carpeting. There was a tissue box tossed haphazardly onto the floor behind the passenger seat with what looked like a bloody fingerprint on it. Investigators collected and bagged the tissue box as well as some sort of colored rag found in the backseat.

In addition to what appeared to be blood on and inside the car, investigators dusted for fingerprints, collecting dozens of latent prints for later comparison. Among the other evidence collected from inside the vehicle were a few invoices for a male patient at the dental office where Penney worked.

Outside of the car, a trail of what appeared to be blood was beginning to tell a story for investigators trying to make sense of what happened. The trail of droplets looked like it followed a path from the car to a stairwell that connected the 9th and 10th floors of the garage. On the 7th floor, investigators found a set of car keys on a white key holder, and not far from the keys, they collected a white handkerchief, wet with what was believed to be blood. The blood-like trail of droplets extended as far as the stairwell landing on level 5B.

Side note, you’ve heard me refer to the reddish stains on the car, tissue box, and other pieces of evidence as “what appeared to be blood” and “what was believed to be blood” and “blood-like” because in terms of homicide investigations, nothing can be assumed or confirmed until forensic science proves that the red stains were, in fact, human blood.

As technicians carefully collected the ample evidence in and around the Buick and the garage, detectives simultaneously canvassed the immediate area for potential witnesses.

Lee stated in his book that the ticket booth agent working in the Temple Street garage that afternoon told investigators that a man leaving the garage had handed him a wet parking ticket. It looked like it could’ve had blood on it, the agent said. He reported that the man with the wet ticket sounded like he maybe had a foreign accent, and was a young white man, but not a kid, with long, dark hair and a thin build. As the man pulled out of the garage, he seemed to be in a hurry and drove over the sidewalk as he sped away. Unfortunately, the agent couldn’t recall any concrete details about the vehicle, just that it was a dark colored sedan.

Detectives also spoke to an employee from Malley’s department store, which was attached to the Temple Street parking structure. He told police that he and two other employees were taking their lunch break in the garage when they saw a dark-haired man with a mustache running after a woman through the garage. Detectives made note of his description of the man, which varied slightly from the description given by the ticket booth agent who hadn’t mentioned a mustache.

The circumstances of the homicide – in broad daylight, in a public place – were alarming, but the evidence seemed ample. Investigators worked diligently to make sense of the scene, but they couldn’t have known their early efforts and careful evidence collection wouldn’t until almost three decades later.

Analyzing Evidence

Penney Serra’s body was transported from the stairwell to Yale-New Haven Hospital where an autopsy was immediately performed. According to Lee’s book, the pathologist determined that Penney died as the result of catastrophic internal bleeding following a single stab wound by a thin, sharp instrument that pierced her right ventricle. The doctor would later tell police that according to his estimations, the murder weapon was one and one-eighth inch in width with a minimum length of three inches. It was unclear if the object had a serrated edge. No object matching this description was found at the scene.

Meanwhile, the evidence was being processed in the Connecticut crime laboratory and detectives were following up with witnesses. All the blood-like smudges, droplets, and spatters found on, in, and around the car and other pieces of evidence were determined by the Toxicology Laboratory at the Hartford Health Department to be human blood, a mixture of type A and type O.

Penney had type A blood and so the type O blood at the scene was assumed to belong to her killer, however, both types are very common. Nearly 38% of the US population is believed to have type O, so it certainly wasn’t enough to narrow down the suspect pool without more information.

In addition to testing on the blood evidence, the fingerprints lifted from the car were compared to known people who may have had access to the family Buick. Nearly all of the latent fingerprints collected from the vehicle Penney was driving that day were found to belong to Penney or her family, except for the bloody smudges on the tissue box on the backseat of the car. Those prints didn’t match a single person from Penney’s family. It was possible they belonged to the suspect.

The prints were sent to the Connecticut State Police Identification Unit for further manual comparison to a fingerprint databank as well as the FBI’s fingerprint identification division. It would be a time intensive task. Automated systems for fingerprint comparison wouldn’t exist for several more years. Even after extensive review though, no matches were found.

Police did have a few leads to follow, though. Witness statements and interviews with those who knew Penney best pointed the case in a few directions, beginning with Penney’s ex-fiance.

An Early Suspect

Of all the motives police had to consider, none made any sense. It was broad daylight in a public place when Penney was attacked, her assailant didn’t steal her wallet or her jewelry, and though the car was believed to have been driven by the killer from the ninth floor down to the eighth floor where it was ditched, it didn’t seem any real attempt was made to steal the car. The autopsy showed no evidence of sexual assault.

So what was the point of such a brazen attack? A crime of passion made sense on some level – if no other theory fit the circumstances, could it be a scorned lover? Penney’s former fiance Philip DeLieto was among the first to land on the suspect list.

According to Henry Lee’s book, police executed a search warrant at Philip’s home in East Haven. Investigators found a pair of broken scissors stained with a reddish-brown substance that later tested positive as human blood.

But DeLieto was cooperative with the investigation, and agreed to appear in a lineup at police headquarters. One of the eye witnesses, the employee on a lunch break who said he saw a woman running away from a man in the parking garage, was brought in to view the lineup. As he entered the police station, police inadvertently led the witness past Philip DeLieto. The witness and Phil bumped shoulders and exchanged glances. The witness later picked Philip DeLieto out of the lineup, identifying him the man chasing the woman in the parking garage.

Even before he was picked out of the lineup though, police had strong reason to suspect Philip DeLieto for Penney’s murder. Their on-again, off-again relationship was rocky and Penney had plans to see him that day.

But Philip did have a solid alibi – he’d been working at his family’s luncheonette. His immediate family members vouched that Phil had been there the whole time and customers verified those statements, saying they’d seen Phil at the restaurant, too. Though one witness later modified his statement, noting a 20 minute period when he didn’t see Phil behind the counter, it wasn’t enough to invalidate the alibi. The parking garage was far enough away that the timeline wouldn’t have worked anyway.

What’s more, Phil’s fingerprints were compared to the bloody smudge left on the tissue box inside the car, but it wasn’t a match.

Police may have moved past Penney’s ex-fiance as a suspect early on in the investigation, but Philip DeLieto’s name was still tossed around in public conversation. The greater New Haven community seemed convinced that Philip DeLieto was the perpetrator and that justice had failed to fall on his head because of a rumored cover-up by the police chief, who you’ll remember was Phil’s distant relative. It didn’t matter that he had an airtight alibi and none of the evidence, not even the fingerprints, pointed to Phil. He made sense as the killer to a nervous population that wanted their sense of safety back.

Behind closed doors, the investigation moved forward in search of other possible suspects. Lee wrote in Cracking More Cases that a team of four detectives, in addition to New Haven PD’s Nicholas Pastore who led the team, had a hunch about the colored rag they found on the floor of the backseat in the car. After further inspection, investigators determined it was a rag similar to those used by mechanics. That one clue directed the team to execute a massive canvassing effort – they’d interview all the owners and managers of all the gas stations and auto repair shops in New Haven county to see if they could locate the rag’s owner.

Whether they completed that effort – which would’ve meant visiting over 2500 different shops and gas stations, according to Lee – and whether it provided any meaningful information is unclear. Several months after Penney’s death, police still had yet to make an arrest.

Case Goes Cold

John Serra, Penney’s heartbroken father, grew frustrated with the lack of progress. He decided to launch his own campaign to find his daughter’s killer, one that would cost him tens of thousands of dollars over the remainder of his life. He took out ads in the New Haven Register newspaper.

A typical ad was just a few inches of valuable black-and-white space with a photo of Penney Serra on the left and a few lines of text on the right. It read: Penney Serra, murdered in Temple Street garage, downtown New Haven on July 16, 1973 (daytime). To date, KILLER STILL IN NEW HAVEN AREA!

That last bit, about the killer still being in the area, was in all caps but it hadn’t been proven true by the investigation, not yet.

Later on, John Serra would sue the parking garage for negligence. According to Nicole Simmons reporting for the New York Times, the Temple Street garage had two security guards, but at the time Penney was killed, they were both across the street on a coffee break. John eventually was awarded damages of $200,000.

Kristi Vaughan reported for the Hartford Courant that John checked in with the police department almost daily, whether it was stopping by to talk to detectives face to face, or calling them up to remind investigators he was still there, still waiting for his daughter’s murder case to find a break. He personally offered a reward of $30,000 for information leading to the arrest of his daughter’s killer. He hired a private detective and even consulted psychics.

John drove to the scene of the crime himself, spent hours driving laps around New Haven looking for people with a bandage on their wrist or a scar on their hands because, according to reporting by Nicole Simmons for the New York Times, police believed that whoever killed Penney had injured themselves in the attack, possibly slicing their left wrist near their hand. Penney’s little sister, Rosemary, later described her father’s state of mind as “living a nightmare.”

But despite the efforts by police and John Serra himself, the case went cold. Eleven years passed before a big break came.