From Pedestal to Prison

The blue-blooded history of Nantucket is usually written in trophies and silver spoons, but the story of the Constables, one that until now has yet to be fully told, ended in a federal evidence locker.

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The Constables were not just residents of Nantucket, they were the embodiment of its ideals. They were champions, healers and mentors. But behind the cedar-shingled walls and the trophies of three generations, a rot was festering, one that would eventually culminate in a tragedy so depraved it would shatter the family name and leave a trail of broken lives from the shores of Nantucket to the villages of Southeast Asia.

While the world saw an Ivy League pedigree and athletic brilliance, a federal investigation would eventually unmask William Constable as a calculated predator, revealing that his elite status was merely a cloak for a horrific history of child exploitation.

 

The Titans of the Court

To understand the fall of William "Howe" Constable — known simply as Howe on Nantucket — one must first look at the pedestals upon which his parents stood. His mother, Elizabeth ‘Betty’ Howe Constable, was squash royalty. In the 1950s, she was the most feared woman on a court. A left-handed power player with a clinical focus, she claimed five national titles and eventually became the architect of the women’s varsity squash program at Princeton. The Howe Cup, the pinnacle of the sport, bears her family name.

 

Her husband, Dr. William Pepper Constable Jr., was her equal in stature. A Harvard-educated physician and former Chief of Medicine, he was best known to the public as ‘Pepper’, the legendary captain of the undefeated 1935 Princeton football team. He was known as the Baltimore Bullett because he “plowed into the line like a runaway locomotive,” wrote Norman Macht in Football’s Last Iron Men, an account of Yale’s 1934 upset of Princeton. “A perfectionist, he demanded more of himself than any human being could deliver.” 

 

In the eyes of the Nantucket community, the Constables were the Gold Standard, the kind of family whose lineage felt woven into the very fabric of the island’s history. For decades, Howe Constable appeared to be the perfect custodian of that legacy. A graduate of Northeastern University who settled on the island in his twenties, he was more than just a local contractor, he was a cultural fixture. He spent his early years building stage sets for the Theatre Workshop and working for the Nantucket Historical Association, eventually running a business specializing in the delicate art of historic renovations.

 

He was a man who seemed to connect very well with the vibe of Nantucket. A singer with the NCMC Chorus and a competitive sailor, Constable was often seen at the helm of his 21-foot Alden-designed Nopque. As a founding director of the Nantucket Community Sailing Program and a former Junior Yacht Club Director, Howe was a ubiquitous mentor, widely respected for passing on his maritime expertise to the next generation. Whether he was leading his nieces on expeditions to study the island’s fragile ecology or coaching high schoolers on a tack, he presented the image of a devoted islander, a soft-spoken man whose quick wit and deep roots made him the ultimate trusted neighbor.

 

The Water and the Shadow

The first crack in the foundation appeared on a Wednesday in August 1986. Pepper Constable, then 72, went for a swim near their summer home. He was a man of vigor, a former athlete who knew the currents of the Nantucket better than most. But the ocean is indifferent to pedigree. Pepper drowned that afternoon, his body recovered from the surf, leaving Betty, a widow and 32-year-old Howe, to navigate a world without the looming shadow of the patriarch.

 

In the two decades that followed, Constable maintained the veneer of the respectable islander. He moved through the yacht clubs and the construction sites of Nantucket with the ease of a man who belonged. But beneath the surface, a predatory compulsion was taking root. Between 1994 and 2007, while the island slept through its quiet winters, Howe Constable was traveling. He made annual pilgrimages to Thailand, Cambodia, and Vietnam. To his neighbors, these were perhaps seen as the eccentric travels of a bachelor with a penchant for the East. In reality, they were hunting trips.

During the 1990s and early 2000s, parts of Southeast Asia became known destinations for Western offenders exploiting gaps in enforcement and vulnerable populations. Travel from the United States was relatively routine for those with financial means — commercial flights, short-term visas and repeat entry raised little scrutiny absent a known criminal record.

 

Law enforcement agencies would later describe how offenders operated within those environments. Rather than sophisticated networks, access often came through informal, local channels, areas tied to tourism where poverty, weak oversight and transient populations created conditions where vulnerable children could be approached with little immediate consequence. The interactions were frequently initiated in public or semi-public settings and then moved into private spaces, where the abuse occurred and, in some cases, documented.

 

Constable’s movements fit that broader pattern of seasonal departures from Nantucket during the winter months, followed by returns to a life that appeared, on the surface, unchanged. What made cases like this difficult to detect was not complexity, but separation, and the distance between where the crimes occurred and where the offender lived allowed both realities to exist without immediate collision.

 

The Camera in the Hotel

The end of the Constable legacy began not on a squash court or a football field, but at a Comfort Inn in Hyannis.

 

In 2007, Constable’s predatory actions were finally undone by his own carelessness when he left behind a digital video camera in his room. When staff reviewed the footage to identify the owner, they found video files depicting Constable's systematic sexual assault and rape of dozens of pre-pubescent girls, many "crying, screaming, and gagged”, some as young as seven years old. This prompted the hotel to contact authorities, and under police instruction, the staff maintained a facade of normalcy. When Constable returned to the front desk to claim the device, his admission of ownership served as a self-inflicted trap that led to his immediate arrest. 

Unbeknownst to him, the hotel lobby had been transformed into a silent perimeter as officers were waiting in hiding, watching from the shadows as he walked toward the counter. The moment he reached for the camera, the physical proof of his depravity, the trap snapped shut, and the officers closed in to end his global campaign of abuse.

 

A search of his Nantucket home revealed a library of horror, with the discovery of 79 camcorder cassettes and DVDs, a self-produced archive of his tours through Southeast Asia. The man who coached Nantucket’s children on the water had spent fourteen years destroying the lives of children halfway across the globe.

 

The Final Month

He pleaded guilty to charges related to the production and possession of child pornography involving minors overseas. At sentencing, prosecutors detailed the scope and severity of the material recovered, describing a sustained pattern of abuse documented over multiple years.

In June 2008, Constable sat in a federal courtroom in Boston. He was sentenced to 25 years in prison. The judge ordered a $50,000 fine and a lifetime of supervised release, a sentence meant to ensure he would never again walk the streets of Nantucket as a free man. 

 

But Constable would not serve 25 years. Just two months after his sentencing, in August 2008, the 54-year-old was found dead in his prison cell. The cause of death was later determined to be from natural causes.

The tragedy, however, had one final, poetic beat. Back in New Jersey, Betty Constable, the champion, the Hall of Famer, the woman who had spent a lifetime building a name associated with excellence, was fading. Whether it was the weight of her son’s monstrous revelations or the natural toll of her 83 years, she did not long survive the news of his death. In September 2008, one month after her son died in a prison cell, Betty Constable passed away.

The siblings were left to manage the fallout of a dual inheritance, the prestige of the Howe/Constable athletic dynasty and the radioactive stigma of Constable's crimes. While the Howe Cup still carries their mother’s name in the squash world, and the Pepper Constable name remains legendary in Princeton football lore, the living siblings represent the survival of the family’s original values. They chose the dignity of their own paths. Dr. Catherine "Kacey" Constable Nugent in the field of medical ethics as a professor at NYU, W. Pepper Constable III in the world of international business and real estate in Europe, and Margaret and Elizabeth, who sought more private, creative lives in Colorado and the Pacific Northwest, effectively severing the family’s narrative from the man who nearly burned it down.

 

The Silence of Orange Street

Today, the story of the Constables survives in fragments. The Squash Queen, the Undefeated Captain, and the man whose crimes rewrote the meaning of the name. It’s a story that resists clean resolution. A legacy built on excellence, existing alongside a record of exploitation that unfolded far from the island, but in parallel with a life lived fully within it.

 

It’s a contradictory narrative, one of meritocracy, athletics, the Ivy League, and another of privilege used as a mask for the unthinkable. The Constable name, once synonymous with the Howe Cup and the heights of human achievement, now serves as a haunting reminder that the most polished exteriors can hide the darkest depths.

 

At 39 Orange Street, the house no longer holds the secrets of a dynasty. The story of the Constables is finished, a tragedy in four acts, ending in the cold silence of a prison cell and the mourning of a lost era.