The checkered history and doubtful future of New England’s ‘Alcatraz of the East’

View of the Portsmouth Naval Prison circa 1973. Naval History and Heritage Command

Even nearly four and a half decades into retirement, the Portsmouth Naval Prison looks foreboding as ever. The massive concrete building looms over the opening of Portsmouth Harbor atop a bluff on Seavey’s Island — a head-turning sight for boaters or drivers on the state’s coastal Route 1B across the water.

For both its character and location, the prison was dubbed the “Alcatraz of the East,” a nickname that has only added to its shroud of mystery. Having seen several major wars — and even a young Humphrey Bogart — myths about the intimidating building abound.

“It’s designed to look like a medieval castle,” said filmmaker Neil Novello, who says there were unfounded early rumors of the prison containing a dungeon.


In truth, its history is less dark than it is complicated. Conversely, it’s the future of the building that looks less than bright.

The Portsmouth Naval Prison opened in 1908, after the Navy had kept prisoners from the Spanish-American War on the island in a Revolution-era fortification formerly known as Fort Sullivan.

Novello, the producer of the documentary The Castle, said in an interview that the prison was modeled after its historic civilian counterparts in Leavenworth, Kansas and Auburn, New York. It would eventually house military prisoners from the Navy, Marines, and Coast Guard for offenses ranging from cowardice and desertion to war crimes and fragging.

Despite its name, the prison is not located in New Hampshire but in Kittery, Maine (as is the rest of the federally owned Portsmouth Naval Shipyard), a matter which was finally settled by a 2001 Supreme Court decision following a decades-old border dispute between the two states.

Like Alcatraz, the prison’s island location amid swift-flowing currents served as a natural deterrent to potential escapees.

In her book on the prison, author Katy Kramer writes that the Piscatagua River, fed by seven rivers, has “one of the fastest tidal currents among America’s navigable waters, making it almost impossible for even a strong swimmer to gain headway.” According to Kramer, even in the summer — when the deathly cold New England waters slightly warmed — prisoners were “no match for its ebb and flood currents.”


In 1912, the central castle-like turrets were added to the prison. By World War I, the population reached over 2,000 inmates.

Conditions were rough, according to Novello, who described an “unhealthy relationship” between the guards and prisoners. Inmates were figuratively (and sometimes literally) chained by the prison’s hardline approach. Contraband and criminal activity in the prison were rampant, he said.

Portsmouth Naval Prison complex looking east circa 1918.

It was around this time that Thomas Mott Osborne, an accomplished prison reformer, arrived in Portsmouth — first as a disguised prisoner to investigate and report on the prison’s condition, before taking over as warden in 1917.

Osborne — who was a friend of then-Assistant Secretary of the Navy Franklin Delano Roosevelt dating back to their years at Harvard — worked to institute what were then considered quite progressive reforms at the prison with the goal of rehabilitating inmates, rather than solely punishing them.

With Roosevelt’s backing, Osborne pushed to generally give prisoners more freedom and eventually added amenities including a theater, YMCA, and basketball gym to the prison. Novello said his theory was to have “prisoners governing prisoners.” And according to historian Rod Watterson, Roosevelt himself once even officially signed off on allowing prisoners to attend shows at the Portsmouth Opera House. Eventually, the prisoners themselves were traveling as far as Manchester to perform in self-produced plays, Watterson wrote in his book Whips to Walls.


Novello says Osborne also instituted programs to equip inmates with tools for life after prison — as well as the military. Lessons ranged from the basics, such as writing a check or opening a bank account, to even teaching them about democracy.

Osborne’s reforms were met with resistance among higher-up officials in the military, especially once the war ended.

A July 22, 1921 article in The Boston Globe.

“[The prisoners] are in a home so good that they would not even try to escape,” one Navy admiral said, according to Watterson’s book, of the conditions at Portsmouth under Osborne’s lead.

Despite “record” rehabilitation numbers and successfully defending himself against a Justice Department investigation, Osborne eventually retired under the mounting pressure in 1921. According to a Boston Globe report at the time, the prisoner-elected guards were shortly thereafter replaced by Marines.

Despite Osborne’s efforts, perhaps the most lasting result from the WWI years at Portsmouth Naval Prison was completely unrelated to prison reform — its impact pertaining solely to the face of a Hollywood legend.

According to several accounts, a young Humphrey Bogart was stationed at the prison. Novello says he was a “chaser” for the Navy, escorting convicted sailors to the prison. In one incident, Bogart was reportedly escorting a sailor through Boston en route to Portsmouth when the prisoner tried to escape.

“The guy tried to get away, took his gun, they had a struggle, and the prisoner hit him in the lip with the gun,” Novello said.


The lasting lip scar resulted in “that sort of distinct Bogart sound,” according to Novello.

“It kind of gave him a split lip; put a little bit of an accent on the way he talks,” he said. The origins of the scar have been disputed, but the Portsmouth story appears to be the most widely accepted and continues to be told during local tours.

The prison population again peaked during World War II, surpassing 3,000 inmates at times. In 1944, the Globe reported that the institution was rehabilitating and returning 86 percent of its prisoners to military service. One case of prisoners returning to action even involved another future celebrity of sorts. L. Ron Hubbard, the founder of Scientology, as a Navy captain, trained and led a crew of convicts during World War II.

When the war ended, the prison was also the site of the surrendering of four German U-boats. Captured off the coast of Maine, the submarines had been destined for Japan, according to Novello. However, when the first wave of German crews arrived in Portsmouth, their belongings were looted by the correctional officers.

The German crews’ commanding officer, Friedrich Steinhoff, was even pushed to the point of suicide, according to reports.

“This fellow interrogated the German officer, slapped him around a little bit, and then took him down to Boston and paraded him through the streets,” Novello said. “People jeered and threw things at him.”

Taken to the Charles Street Jail, a civilian prison, Steinhoff slit his wrists with broken glass lenses and was found in a pool of his own blood, according to the Globe. He bled out before officials could transport him to nearby Massachusetts General Hospital.


While there were many escape attempts at the prison — including several attempts to swim across the river and one instance in which a prisoner tried to hide inside a bag of dirty laundry — only one was ever successful, according to the Globe.

During the Vietnam War, a man convicted of selling drugs while AWOL in Okinawa reportedly escaped by cutting through the prison’s iron bars with a hacksaw and crossing the river by sailboat while guards were watching TV.

The prison in 2008.

After housing nearly 83,000 inmates and witnessing four major wars, the prison was decommissioned in 1974 when its dwindling population of 300 was released or transferred. The massive building itself was also failing into disrepair.

“The question was: Was it worth keeping?” Novello said. “The construction material for the most part was banned — the use of asbestos, the use of certain chemicals and lead paint. It’s toxic in there, and that’s besides all the animal waste and the corroding metals.”

After it closed, the looming building sat idle for two decades. In the 1990s, New Hampshire developer Joseph Sawtelle proposed repurposing the south wing as high-tech office space.

“He plans to resurrect the old brig as a Fortress of Technology,” the Globe reported in 1999.

Sawtelle had also led the local effort to save the USS Albacore, turning the decommissioned submarine into a museum. Eventually, the Navy reached an agreement to lease the entrepreneur and philanthropist the former prison.

However, Sawtelle died soon-after in May 2000 — and with him any immediate hopes of reviving the so-called Castle.


“They had started to carve out sections and I think even had the blueprint of the design they wanted,” Novello said. “But when he passed away, the contractor who was doing this could not find another backer.”

Tightened security at the shipyard after the September 11, 2001 attacks made proposals to redevelop the prison — located at the opposite side to the island’s access point — even more difficult. Meanwhile, the building itself continues to descend further into disrepair.

“There is a huge amount of rehab that needs to be done before the facility could be used,” Peter Bowman, a former commander of the Portsmouth shipyard, told the Associated Press last year.

“Entropy continues to take its toll on this iconic building,” he added.

The third and most recent attempt to redevelop the prison was officially abandoned last September, after the Navy rejected three private-sector proposals.

“After an open and competitive solicitation process and a thorough review of submitted proposals, the Navy was unable to conclude that an economically viable proposal meeting all Navy conditions for selection had been submitted,” Navy spokesman Todd Lyman said in an email.

According to Lyman, the Navy is “not currently” entertaining any proposals to revive Building 93, as the former prison is officially known. A portion of the building is now being used for storage, he said.