America’s kindest prison sat on this New Hampshire naval base for four years

Osborne’s Undercover Mission to Transform Portsmouth Naval Prison

In 1917, Thomas Mott Osborne did something no one would expect. He went to jail on purpose.

Already known for fixing broken prisons, Osborne went undercover at Portsmouth Naval Prison to see its problems firsthand. What he found was awful – fights, crime, and guards who made things worse.

Soon after, he took charge as the only civilian ever to run this military prison. He fired bad guards, opened up cells into dorms, and let inmates govern themselves through the Mutual Welfare League.

The results were clear: just eight escapes out of 6,000 men, with 4,000 returning to Navy service. Sadly, politics killed this bold experiment by 1921.

The stone fortress still stands in New Hampshire as a silent witness to what might have been.

FDR Helped Bring a Civilian to Fix the Navy’s Worst Prison

Navy Secretary Josephus Daniels asked Thomas Mott Osborne to check out Portsmouth Naval Prison in 1916. Assistant Secretary Franklin Roosevelt suggested this bold move.

The prison held Navy, Marine, and Coast Guard inmates for crimes from skipping duty to serious war crimes. People called it the “Alcatraz of the East” because of its castle look and strong tides that stopped swimmers.

After 1914, Portsmouth became the Navy’s main prison, holding up to 2,295 men during World War I.

This Prison Reformer Went Undercover as an Inmate

Osborne and two friends took a big risk in 1917 – they entered Portsmouth as fake prisoners to see real conditions firsthand. What they found shocked them.

Crime ran wild throughout the facility. Guards had poor training.

Fights broke out constantly as different types of offenders mixed together. Inmates wore shameful uniforms and followed senseless rules.

The place felt more like a medieval dungeon than a modern American facility.

The Navy Broke All Rules by Appointing Him Commander

Secretary Daniels stunned military leaders in July 1917 by giving civilian Osborne the rank of Lieutenant Commander and putting him in charge of Portsmouth Naval Prison.

No civilian had ever run a military prison before in American history.

Osborne came with great experience from his work at Auburn and Sing Sing prisons, where he created the “Mutual Welfare League” system. Roosevelt strongly backed him when military leaders complained.

Prisoners Started Running Their Own Prison

Osborne quickly fired the guards who worked inside the main compound. He replaced them with committees that inmates elected themselves.

These prisoner groups handled discipline problems, organized business matters, and planned entertainment. His approach let prisoners govern themselves instead of facing harsh control from guards.

Osborne believed that “liberty alone fits men for liberty” and put this idea into practice every day at Portsmouth.

The Castle Prison Turned Into Something Unrecognizable

The main cell block changed completely under Osborne’s watch. Workers knocked down walls between cells to create open dormitory spaces.

They added a theater, a full YMCA facility for workouts, and basketball courts. Roosevelt even approved letting some prisoners attend shows at the Portsmouth Opera House in town.

Prison theater groups traveled as far as Manchester to perform their own shows.

Inmates Learned Everything from Banking to Democracy

Classes at Portsmouth taught practical skills many inmates never learned before. Men practiced writing checks, opening bank accounts, and managing money.

They discussed democracy and civic responsibility daily. Vocational training prepared inmates for jobs after release.

Every program aimed to give these men tools for success once they left prison, whether returning to civilian life or rejoining military service.

Almost No One Tried to Escape This Open Prison

The numbers tell an amazing story about Osborne’s three years in command. Out of roughly 6,000 men held at Portsmouth during this time, only eight tried to escape.

About 4,000 prisoners successfully returned to active naval duty after serving their sentences. These results beat anything achieved at other military or civilian prisons.

Secretary Daniels praised Osborne for “mending rather than breaking men” through his revolutionary approach.

Military Leaders Hated Seeing "Criminals" Get Second Chances

Vice Admiral William S. Sims led the fight against Osborne’s reforms.

He complained about “troublemakers” coming back to serve on ships. Other officers grumbled that conditions at Portsmouth were too comfortable.

One critic said prisoners lived in a “home so good that they would not even try to escape. ” Traditional military minds saw the reforms as “coddling” men who deserved punishment.

This opposition grew stronger after World War I ended.

The Government Investigated His Unconventional Methods

Pressure from senior officers forced a formal Justice Department investigation of how Osborne ran things. Accusations included bad management and claims about inappropriate activities among prisoners.

Roosevelt personally led an on-site team to look into these claims.

Though Osborne defended his methods and proved the charges wrong, the political heat became too much to handle.

President Harding’s Team Killed the Experiment

Warren G. Harding picked Edwin Denby as his new Navy Secretary in March 1921.

Denby quickly shut down the Mutual Welfare League program. He brought back harsh discipline.

Marines replaced the prisoner-elected guards throughout the facility. Osborne had already quit in March 1920, seeing what was coming.

His departure ended the most forward-thinking military prison reform experiment America has ever seen.

The Navy Threw Away a Program That Actually Worked

Portsmouth’s experiment represented the high point of Progressive Era prison reform ideas applied to military justice.

When officials terminated the program, they chose punishment over rehabilitation despite clear evidence of success.

Osborne continued fighting for prison reform through the National Society of Penal Information until his death in 1926.

The military justice system missed a golden opportunity to maintain a humane approach that had achieved record-breaking rehabilitation rates.

Visiting Portsmouth Naval Prison, New Hampshire

Unfortunately, you can’t visit the actual Portsmouth Naval Prison where Thomas Mott Osborne ran his groundbreaking prison reform experiment from 1917 to 1921.

The abandoned building sits on restricted federal property at Portsmouth Naval Shipyard in Kittery, Maine, with no public access since 1974. You can catch distant glimpses from Portsmouth Harbor boat tours.

For more about Osborne’s revolutionary “Mutual Welfare League” program, check Portsmouth Public Library for occasional history presentations or visit Portsmouth Historical Society for related artifacts.

This article was created with AI assistance and human editing.

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