Friday, May 27, 2016

Escapes from Alcatraz - a History of Swimming from and Escaping from Alcatraz

When I was young, the common impression was that “escape from Alcatraz” had always been “Impossible.”  The mystique was bouyed by popular films like 1979’s Escape from Alcatraz, and periodic TV, newspaper or magazine bits about Morris and Anglin’s notorious Alcatraz jailbreak and disappearance in 1963.  The temperature was too cold they said, the sharks too numerous, the currents and tides too unpredictable; no one could possibly survive such a swim without freezing to death, getting eaten by sharks or being swept out to open sea.

Today, however, thousands of swimmers swim from Alcatraz to San Francisco or Marin County every year, with the help of modern swimwear technology, an army of safety boats and lifeguards, and secure in the knowledge that thousands of others regularly make the same swim and live to tell about it.  Events like Escape from Alcatraz, The San Francisco Triathlon at Alcatraz, Escape from the Rock, and Sharkfest have taken a bite out of Alcatraz’s reputation as an un-escape-from-able fortress. A close look at Alcatraz’s history, however, shows that its reputation had already taken a big hit during the months before it closed; and may have been largely bluster from the start.

Although the federal government still claims that no one ever successfully escaped from Alcatraz during its three decades as a federal prison, John Paul Scott made it to San Francisco alive in late 1962:

Scott . . . was near death when he washed ashore at Fort Point just inside the Golden Gate Bridge and nearly three miles from the prison . . . .  Scott’s spectacular if futile swim from Alcatraz island destroyed once and for all the official position that escape from Alcatraz is impossible.  And it added strength to the supposition that other escapers have made it safely to shore.  Escapers such as Frank Lee Morris and John and Clarence Anglin, who are known to have entered the water last June.  Escapers such as Theodore Cole and Ralph Roe were last seen Dec. 16, 1937.  These five have never been found.[i]

Alcatraz federal prison closed for good, four months after Scott’s attempt. 

It is a testament to the human spirit’s ability to forget inconvenient truths that the myth survived for as long as it did.  The myth had been called into question decades earlier, at the very moment it was being  transferred to the Justice Department after seventy years as a military prison:

The scheme [(transfer of Alcatraz to the Department of Justice)] probably was sold to Washington on the strength of the myth that escape by swimming is impossible because of the currents that swirl around and around the island as they do in the case of the French Devil’s island off the Guiana coast.

Legend says that former warden at Alcatraz discouraged attempts at escape by offering a bathing suit and chance for liberty to each new arrival.  Those who accepted are supposed to have battled the currents vainly until fished out.

Now that myth has been blown up by the girl swimmer who stepped off at Alcatraz the other day and reached the mainland without difficulty.

Madera Tribune (Madera, California), October 21, 1933, page 2.

While the nation discussed Alcatraz island, in San Francisco bay, as a place where hardened criminals could be kept by Uncle Sam with no chance to escape, “Babe” Scott, 17, upset these theories by swimming from the island to San Francisco in 47 minutes.
Healdsburg Tribune (Healdsburg, California), October 23, 1933, page 2.

“It was easy,” said Anastalia (Babe) Scott.  She swam the one and one-half miles stretch in 47 minutes.

Her father is an army sergeant stationed on the island, now a disciplinary barracks, and she had planned to try the swim for years, she said.

Delaware County Daily Times (Chester, Pennsylvania), October 18, 1933, page 2.

The mere fact that the myth developed in the first place is surprising, since “Babe” Scott was not the first person to make the swim; much less the first young woman.  More than two decades earlier, the Corosio sisters swam out to Alcatraz and back.[ii]  

The San Francisco Call, September 5, 1910, page 8.
A couple years later, Tina Ihrmark, the nineteen year-old wife of UC Berkeley’s swimming coach, successfully swam to Alcatraz; sadly, she was aiming for Alameda:

The Sacramento Union, May 20, 1912, page 3.

A swimming club in San Francisco organized out-and-back races to Alcatraz as early as 1897:

San Francisco Call, June 1, 1897, page 7.
And a doctor from Alameda swam from Black Point in San Francisco to Oakland in 1882:

The Daily Bulletin (Honolulu, Hawaii), August 24, 1882, page 2.

The swim may have been “easy” for well-trained, highly-conditioned athletes like “Babe” Scott and Tina Ihrmark, but it was a different story for hardened criminals or young Army deserters, at night, with no safety boat, and with no opportunity to train for the swim.  Of course, the odds were against them, and many people died making the attempt, but escape was never impossible.  

Before Alcatraz became a federal prison, at least twenty-three people successfully escaped from Alcatraz military prison; several of them by swimming.  The first escape from Alcatraz, in 1868, was a swimmer – and he survived.

Escapes from Alcatraz

To be fair, escape from Alcatraz was always difficult; and its reputation as a place from which escape was difficult and potentially deadly was well deserved.  During its sixty-five years as a military prison, no fewer than 51 people “escaped” from Alcatraz one way or the other; of whom twenty-three were successful, nineteen were recaptured during the attempt,[iii] and one was never accounted for.  Six men died making the attempt; all of them swimmers.  Not great odds, I suppose, but perhaps worth it for young men stuck out on the “Rock”.

The first escape was in 1868, its first year as an officially designated military prison.[iv]  The last successful escape I could document was in 1924, nearly ten years before it was transferred to the federal prison system.  The escapees included German POWs from World War I and a convicted deserter from Philippine-American War who may actually have been more of a hero, and whose escape may have saved him from a death sentence (President Roosevelt commuted his sentence from death to life in prison after his escape).  The various means of escape included being mailed out in a box, paddling away in a butter tub, and simply walking onto a ferry wearing stolen uniforms or carrying forged orders.

The most dangerous escapes involved swimming.  Of twenty-seven people involved in the fifteen escape attempts involving swimming, or floating on improvised floats or rafts, seventeen were recaptured during the attempt.  Of the ten others, three reached dry land, six died, and one was never accounted for.

Escape was dangerous – especially for the swimmers – but it wasn’t “impossible.”

The Swimmers

In 1868, three soldiers named King, Frank and Swaney attempted to swim to freedom from Alcatraz; only one of them made it – perhaps the first “escape from Alcatraz.”  The one who made it had a sense of humor:

Big Swimming. – A San Francisco dispatch of Aug. 16th says:
A few days since three soldiers named Swaney, Frank and King, deserted from Alcatraz Island, and undertook to swim to Lime Point [(at the northern end of the Golden Gate)], a distance of four miles.  The sea was boisterous, but the extraordinary and unprecedented feat was actually accomplished by King, in six hours and a half.  Frank was drowned and Swaney was picked up off Fort Point [(at the southern end of the Golden Gate)], after having been in the water over five hours.  They all started with a small raft of logs, which they used as buoys.  King wrote from San Jose to the Colonel commanding Alcatraz Island, announcing his safety and sending his compliments.

Idaho Semi-Weekly World (Idaho City, Idaho), August 26, 1868, page 4.

In 1900, two swimmers were less successful: 

San Francisco Call, June 2, 1900, page 11.

Joseph Caulfield and Michael Tracy, two military convicts now confined in a dungeon at Alcatraz Island on a bread and water diet, have just passed through an adventure of attempted escape full of desperate chances and signalized by an utter disregard for personal safety. . . . [After escaping onto the roof through an unused chimney,] Caulfield and Tracy dropped to the ground, dodging the sentries and keeping well under cover until they reached the bellhouse steps on the south side of the island.  Here they found a board float which was moored fast.  This they succeeded in cutting adrift.  Nothing but large shingles was at hand, so they boarded the float, using these as paddles.

Out on the dark waters of the bay the two desperate men worked their way with their improvised paddles and an opportune float.  For several hours they excerted every effort to work their way toward the city, but they got caught in an eddying current and could make no headway.

Drenched to the skin, their strength spent by their arduous labors, they were discovered by a guard at 4 a.m. just as the day was dawning.  At the time they were floating hopelessly in the swirling tide, and a few shots from Guard Jorgensen wrought a desire on the part of the convicts to return to their island prison.  After a short time the two men on the float landed and were placed in a dungeon.

In 1906, prisoners, Arthur Armstrong, George Davis, Thomas Stinnatt and George Brossman made a similarly futile attempt to paddle away from prison in an old butter vat:

The San Francisco Call, April 5, 1906, page 1.

In 1907, August Stillke, paddling on a wooden plank, nearly made landfall at the Union Street ferry dock on a wooden plank; before being struck by a ferry boat in the dark.  After his rescue and a few hours in an emergency hospital; he was sent back to Alcatraz. 

The San Francisco Call, October 23, 1907, page 16.

In 1927, John Duckworth and Sam Kilgure swam to within about one mile of the Marin County shoreline (three miles from Alcatraz) when they were more politely pulled from the water by another ferry.  The pair were reportedly still “going strong” when they were picked up.  When asked why they tried to escape, Duckworth responded like a bored summer guest changing cottages; “Well, we got tired of staying on Alcatraz and wanted a change.”  Kilgure, a “tough character,” gave a more situation-appropriate response; “I decided to do or die when I escaped from the island. . . . [and would] try it again at the first opportunity.”

Sausalito News, October 8, 1927, page 1.

In 1920, Charles Roberts, J. J. Howington and E. R. Hannah made it all of the way to Goat Island (Yerba Buena Island between San Francisco and Oakland; a distance of more than three miles), before being picked up by authorities.  “The three were clinging to the wreckage of a raft on which they had made their escape from Alcatraz Island.  They were exhausted and were taken to the emergency hospital.[v] 

Two men floated off on a ladder in 1929 and were picked up in the bay.[vi]  In March of 1930, three swimmers swimming toward Marin County called for help when they foundered in the cold water; they were rescued by an army launch.[vii]

On June 24, 1930, Jack Allen, 23, was reported missing from Alcatraz.  He was never seen again.  Officials were unsure whether he made it ashore or drowned on the way; but he had apparently prepared for the swim like a real long-distance swimmer.  His pants, left behind on the island, were found to have lard in the pockets. [viii]  Long distance swimmers still smear grease on their bodies to keep the cold water off the body, and to provide a small degree of thermal protection.  Who knows, maybe he made it.

Harry Rodgers’ fate, however, is known.  In April 1932, he may have been the last person to attempt a water escape from Alcatraz during its time as a military prison.  Guards saw him enter the water; and watched him slip under the water about 400 yards from shore.  He never came up.

Others died too. Patrick O’Leary gave his life to escape prison, despite his elaborate, stealth raft:

San Francisco, Oct. 10.- The hungry tides that lap the shores of Alcatraz island make it difficult to escape from the federal prison there.  Patrick O’Leary knew it, for that is the reputation of the prison the soldier calls “The rock,” wherever United States soldiers are, but O’Leary made the attempt.  Today he is dead.  The slackened ebb left his body today on the Oakland water front.  He had died of exposure battling with the flood.

Unusual ingenuity and daring had not availed.  O’Leary cut the bottom from a tool chest, all except one plank.  It made a covered ark, in which he could ride astraddle, his head and body shielded from observation, his legs free to swim.  Two small air-tight kegs, attached at either side of the chest, served as sponsoons.

The contrivance did not fail, but the prisoner’s strength did.  He was not sighted and he did not sink, but he could not make headway against the tide.  He was clad only in his underclothes and the chill of the ocean steadily drained away his vitality.

Sacramento Union, October 11, 1914, page 28.

Claude Ely died in 1916; but his partner survived – he was picked up on a rock near the island after foundering in the fog on a drifting log:

San Francisco, February 20. – Two military prisoners made an attempt to escape from Alcatraz last night by swimming, an attempt that ended in the death of one of the prisoners and the surrender of the other.

The Hawaiian Gazette (Honolulu), February 22, 1916, page 5.

A report of the drowning of an unnamed prisoner in 1921 leaves open the possibility that there was yet another escape.  The report referred to him as “one of the prisoners who recently escaped from Alcatraz prison.”[ix]  I do not know what happened to the other one.

Not all swimming escapes were futile.  In addition to prisoner King, who taunted his commanding officer after his escape in 1868, two others survived the ordeal and successfully escaped in extraordinary fashion.


In November 1908, a prisoner named Squires swam to freedom with some unintentional assistance.  During his swim from Alcatraz, Squires was picked up by a passing barge as he was being swept out to sea.  The story might have ended there, but the barge was en route to Monterey, home to a large Army presidio.  The captain of the barge figured he could just as easily deliver the prisoner to authorities in Monterey and still stay on schedule.  What could go wrong? 

Before the barge arrived in Monterey, Squires slid into the bay, swam ashore and was never heard from again.  


The most surprising thing about Leonard Wilmore’s daring swim from Alcatraz to Oakland in November 1901 is that it may not have been his most dangerous escape.  Before he ever arrived in Alcatraz, he had already made two harrowing escapes under fire during his service in the Philippine-American War; each time escaping from one army and its death sentence, and toward another army and another death sentence.  His final escape from Alcatraz was not made under fire, and was not made in the direction of a second death sentence.  The escape from Alcatraz may even have saved his life.

Leonard Wilmore was born in Philadelphia in 1879; the son of a white doctor and a half-Black, half-Native American mother.  He attended Missionary High School until the age of 10, when he ran away from home and eked out a living in the horse-racing business for many years.  In 1898, he found himself in Lexington, Kentucky with no job prospects and on an extended string of bad luck.  Just in the nick of time, the Spanish-American War broke out; he enlisted in the United States Army.

Upon enlistment, he was assigned to the 25th Infantry Regiment – the Buffalo Soldiers.  After a brief time at Fort San Carlos, Arizona, he was shipped out to the Philippines, where he was stationed at “Eba Sanbalos” (Iba Zambales) on Luzon.  This film clip shows General Burt leading elements of the 25th Regiment on their return from Mount Arayat (near Iba Zambales) in 1898.  It’s unlikely, but possible I suppose, that Wilmore might be somewhere in the group.

At Iba Zambales, Wilmore frequently served as a scout and sniper.  He was such a keen shot, and caused so much damage to the Filipino rebels, that they put a bounty on his head – dead or alive; which makes it even more remarkable that he would “desert” his Regiment and join the rebels when he found himself in trouble with the Army.  The trouble began, as it often does, with a game of three-card Monte.

One night, Wilmore sat down with Privates Hart and Thurston in the Regimental barracks to play what he believed was a friendly game of three-card Monte.  Three-card Monte is a “gambling” game (usually just a con game) in which players (usually a mark) try to identify which of three overturned cards is the Queen of Hearts after being shuffled around by the dealer; like a shell game, but with cards. 

Wilmore, a veteran of the racetrack and likely no stranger to gambling schemes, said that he thought the game was being played for fun, among friends; not like a real con as it would normally be played on the street.  After Thurston made a “foul lay,” Wilmore complained:

“We had been playing a friendly game, and I did not much care whether he had dealt foul or not, but I don’t like a man to be unsportsmanlike. 

A bystander named Weedy called Wilmore an easy mark, and an argument ensued.  Weedy loaded his rifle and moved to point the gun at Wilmore, and Wilmore drew his pistol in self-defense.  Wilmore fired first; killing Weedy before he could bring his rifle to bear.  Another man drew a sabre and attacked Wilmore from behind; cutting him in the shoulder.  Wilmore wheeled around and shot him:

He staggered out on to the veranda and toppled over the railing to the ground below, dead.

Wilmore ran from the scene.  He did not run away; he ran straight to General Burt’s office to set the record straight.  He was not a murderer; he fired in self defense.  At trial, however, the witnesses turned against him, and he was sentenced to death for a double-murder. 

While waiting for his conviction to be affirmed, Wilmore made his escape.  He broke the latch on his door; knocked down one guard, and made his way across a three hundred-yard clearing, hoping to make it into a rice field before he was shot by soldiers pursuing him from behind.  After he disappeared into the rice field, his training and experience as a scout came in handy.  He evaded capture, while staying close to town, for several days; hoping to steal a boat, go down river, and ultimately reach China.  But his plans changed when he was surrounded by a band of Filipino soldiers.  

The rebel commander told him that he could not leave the country; and that he would spare his life, but only if he agreed to join the rebels.  With no better option at hand, Wilmore assented.  His loyalty to the cause was not questioned, in part because they knew of his tenuous status in the American Army.  As a result, and because of his military training and experience, they made him a “captain in their much-officered army.” But his loyalties had not really changed; he took advantage of his new position and authority to act as a double-agent, sending valuable intelligence and rendering other assistance to the Americans:

I became a rebel only in name, however; in reality I was a spy for the Americans, and was able to help them even more while supposed to be a deserter and a renegade than I had ever done while a member of my company.

I did not abuse [my authority as a rebel officer], however, by doing my countrymen any harm; in fact, I used every means I could to help them.  I was able to do this through the assistance of an ex-sergeant named Kearney, who had formerly belonged to my regiment, but had left the army and married a Filipino woman.  She was a native princess or noblewoman of some kind, and the Filipinos regarded her house as their head-quarters for hatching treason against the hated Americanos.  Kearney, while pretending that he was in sympathy with the Filipinos, was in reality heart and soul with the Americans.  So was I, although I knew only too well that I had no hope of receiving any benefits from them.  Between us, however, Kearney and I managed to keep our countrymen posted regarding the various secret expeditions of the enemy.  Often and often I have warned the Americans of ambuscades and acts of treachery prepared for them by the Filipinos.

Leonard Wilmore, “The Convict’s Story,” Wide World Magazine, Volume 18, Number 104, November 1906, page 169.

After five months in the rebel army, Wilmore eventually got on their bad side.  His commanding officer sentenced him to death for helping other United States soldiers escape rebel custody.  While awaiting execution, he and another American named Robinson made a mad dash through the jungle; where they were pursued for several nights, while exchanging fire with their pursuers.  Wilmore and Robinson eventually separated; hoping that it might make their chances better.  When Robinson was recaptured, Wilmore killed the two rebels who had him in custody, and returned Robinson to his unit.  Wilmore continued on, surrendering to General Burt and the 25th Regiment in Iba Zambales. 

Wilmore’s account of events, for the most part, appears to be true.  Even President Roosevelt believed the story.  On January 3, 1902, Roosevelt signed an order granting Wilmore clemency, commuting his death sentence to life in prison, on the strength of recommendations by the Commander of the Department of the Army and the Secretary of Defense.[x]  Roosevelt signed the clemency order six weeks after Wilmore escaped from Alcatraz – the hard way – by swimming to Oakland.

On the night of November 16, 1901, after only two weeks at Alcatraz, Wilmore and another prisoner scrambled over a wall when the guards were not looking.  They hid in a shed until nightfall.  When darkness came, they found a wooden ladder (or staircase) to support them during the swim.  But shortly after entering the water, the ladder sank – taking Ernest along with it.  Wilmore made it back to shore on Alcatraz, where he found a board, reentered the water and emerged hours later, incredibly, in Oakland – a distance of about six miles.  

When Wilmore surfaced in Hawaii two years later and claimed to have swum from Alcatraz to Oakland, an Oakland newspaper recounted Dr. Riehl’s 1882 swim from Black Point to Oakland for skeptical readers:

A negro convict at Honolulu has written an account of his adventures before reaching the islands.  According to this statement he escaped from the military prison at Alcatraz and with a companion started to swim to Oakland.  The undertaking was too great for his companion, who was drowned, but he succeeded in reaching the shore after being in the water for eight hours, and made good his escape.  The fact that he felt attracted toward Oakland rather than towards San Francisco shows that he must have had some good still remaining in him, and causes us to feel an unusual interest in his career.  The exploit which he describes is a very possible one, and recalls a similar one that occurred over the same course several years ago.  When the steamer Escambia was lost outside the heads in calm weather and a number of her crew drowned, a well known physician in San Francisco asserted that the loss of life was unnecessary; that every man, especially if he were connected with the sea, should be able to swim the four or five miles necessary to reach land. [(Fourteen people lost their lives when the Escambia went down on June 19, 1882.)]

His statement was challenged and he agreed to prove that such a thing was possible.  Clad in his ordinary clothes he sprang from a boat, a mile west of Alcatraz, and finally left the water at the end of Oakland wharf, having been swimming for six hours.  The swimmer was nearly exhausted at the end, as he had been swept far out off his course by the tide.  But his success in proving his point shows that a convict might make a similar swim and reach the Oakland shore, especially when freedom was the prize. – Oakland Enquirer.

The Hawaiian Star, April 1, 1903, page 8 (citing an article published in the Oakland Chronicle).

Soon after his escape, Wilmore signed on as a crewmember with the whaling ship, California, under the name Leonard Palmer.  After seven months cruising Chinese and Japanese waters, he became ill and was let off the ship at Hokadate, Japan; where he spent two months convalescing in a hospital.  After a short trip to China, the American Consul at Yokahama arranged transportation for him to Honolulu, where he arrived in August of 1902.  Weak from sickness, and short of money, he fell in with a gang of highwaymen to earn some money for passage back to the mainland.  He was caught, arrested, convicted, and sent to prison on Oahu with a twelve year sentence for highway robbery, all under the “Roger James.”  He eventually confessed his true identity to the warden, but only after Sergeant Bates, the man who had escorted Wilmore to Alcatraz two years earlier, recognized and identified him.[xi] 

Years later, when Wilmore was released from a state prison in Hawaii after serving time for highway robbery, Wilmore received what amounted to a de facto pardon; the military authorities did not demand his return to prison.

Other Escapes

Not everyone who escaped from Alcatraz were swimmers.  But many of them made equally elaborate or dramatic, if less dangerous, exits from Alcatraz.


In the largest and most successful prison break in Alcatraz’ long history, four prisoners were escorted from the prison onto a waiting ferry on the strength of forged release orders:

The officials at army headquarters are vainly attempting to get a trace of Joseph White, John L. Moore, Cornelius Stokes (colored) and James Darling (colored), who escaped from Alcatraz prison a week ago to-day on forged orders remitting their sentences, which amounted to about two years in each case.  Major Morrow, judge advocate, and Major Williams, assistant adjutant general, assert that their signatures were forged to the documents.

The San Francisco Call, October 14, 1903, page 14.

The base judge advocate had neglected to follow a system of double-checks that would otherwise have exposed the unexpected set of false orders before their release. 

Shipped Out

In 1900, Jesse Adams found a novel way of leaving the island undetected – he had himself mailed out in a crate – and it worked:

Jesse W. Adams, a military prisoner confined at Alcatraz, has gained his liberty.  He chose a novel means of escape, leaving Alcatraz as merchandise inclosed in a wooden box.  A blx marked “Handle with care” arrived from Alcatraz on the government boat McDowell on its last trip to the Presidio.  It was addressed to the general hospital, and landed at the wharf preparatory to beign transferred to the hospital later.  The wharfmaster found when he came to open it that the box had been broken open and was empty.  Inquiry at Alcatraz showed that one of the 10-year-term prisoners was missing.  How the box was shipped and how the man effected his escape are a mystery.  The box was exceedingly small, being only one and a half feet wide and three feet high.

Rock Island Argus (Illinois), October 6, 1900, page 4.

Frank Holt did the same thing a few years later:

The San Francisco Call, January 12, 1902, page 19.

Frank Holt, a trusty at Alcatraz, serving thirteen years for desertion, cleverly escaped from the island yesterday morning in a large wooden box.  Edward P. Timmons, who was released from Alcatraz about the time that Holt escaped, is being detained by the local police as an accomplice.

A few weeks later, a copycat attempt failed.  A recently discharged Army cavalryman from Oswego, New York, tried shipping himself home when his money was about to run out.  He had had $700 in his pockets when discharged from the Army, but couldn’t find any steady work.  After going to Hawaii looking for work, he returned to San Francisco and started playing the horses when his funds got low – which naturally made them get even lower.  And no, he wasn’t in F Troop, as you might expect; he was in A Troop:

Harry M. Prouse, a former corporal in Troop A, Eleventh Cavalary, imagined that he could travel as freight in a packing case from this city to Chicago.  It was lucky for him that he was discovered before commencing the journey.  He is now being detained at police headquarters until Captain Seymour, who has interested himself in his case, can procure proper transportation for him. . . .

He . . . bought a two weeks’ supply of provisions, including tins of sardines, salmon and sausages, some raisins, a piece of cheese, a demijohn of wine and two pounds of crackers.  He also filled two other demijohns with fresh water.  Two of the boards [in the container] were fixed on the inside with clamps so that Prouse could open them and make his way out of the packing case when the chance arose.

 The San Francisco Call, January 29, 1902, page 7.

German POWs

In 1917, German POWs, perhaps civilian merchant seamen caught up in the conflict, were held at Alcatraz.  Two of them went on what may have been more of a joyride or sightseeing tour than a bona fide escape attempt:

After escaping from internment on Alcatraz island and cruising about San Francisco bay all morning, Captain C. B. Rauch and Engineer Lorenzo Lau were found and recaptured 11 o’clock by a revenue cutter. . . .

After the recapture of the men, it was announced that all interned German members of steamship crews will be taken to an eastern camp, and will start tomorrow.

Red Bluff Daily News (Red Bluff, California), October 17, 1917, page 1.

Stolen Bonds, Cash and Uniforms

The following year, L’Estrange Bach and Carl Zirker took a more forceful route; they stole uniforms, bonds and cash (totaling $700) from the trunk of an officer’s car, and walked onto a government tugboat dressed in the stolen uniforms.[xii]

Blended in with Visitors

In 1924, three prisoners made a more brazen exit:

Roy Kennison, Basil Mann and Edward Lay are still at large after escaping from Alcatraz island military prison last night.
It is believed they mingled with the guests at an entertainment and escaped to the mainland on the visitors’ boat.

Madera Tribune (Madera, California), October 9, 1924, page 1.

The “entertainment” that Kennison and Mann used for cover is perhaps one of the most surprising aspects of life at Alcatraz military prison: 

Once a month, with the consent of the commandant, the prisoners are allowed to give an entertainment.

The soldiers on the island are charged 10 cents admission and visitors from the city are charged 25 cents.  The proceeds go toward buying odds and ends for the prisoners not in the prison fare.

The San Francisco Call, August 19, 1898, page 16.

The prisoners’ “entertainments” had also played a role in a successful three-man escape twenty-five years earlier.

Stole the Commandant’s Boat

The San Francisco Call, August 19, 1898, page 16.

In August 1898, H. R. Beale, John Meredith and Edgar M. Sweeney escaped from Alcatraz in a small rowboat belonging to the son of Major Kinzie, the commandant of the prison.  They made their escape while rehearsing in the library for one of those monthly “entertainments.”  Although the boat dock was guarded, they circled back around the entire island, and came up from behind the guard.  They were able to get into the boat, launch it, and get a sizable head-start before they were discovered.  They were pursued by a five-oared boat, but never caught.[xiii]

Multiple Escapes

One man escaped from Alcatraz not once, but twice.  He was recaptured twice as well; but only after extended periods of freedom.

In May 1890, two prisoners stole a rowboat and got a two mile head start before they were discovered.  Although pursued by guards in a commercial steam-powered ferry (the government’s own steamer was in for repairs), they got away without being caught.[xiv]  One year later, the two were picked up in Sacramento.  Blame it on the booze:

While Bennett was drunk in Sacramento he betrayed his identity, and was arrested and taken back to Alcatraz.[xv]

The Record-Union (Sacramento), February 26, 1892, page 1.

The Morning Call (San Francisco), September 2, 1891, page 3.

Six months later, Bennett was up to his old tricks again:

Two prisoners gave the guards the slip at Alcatraz last night, and made their escape from the island.  Their names were Kelly and Bennett, and both were under sentence for desertion.  A few days ago both pleaded sickness and were sent to the hospital.  They were evidently not very ill, as they made wonderfully quick time in getting out of the way. . . .  The alarm-bell was sounded, and in a moment the island was aroused.  Scouts were sent out in every direction, and in a very short time the rock was entirely surrounded by soldiers.  Up to noon to-day, however, no trace was discovered of the missing men, and it is presumed that they got off the island.

The Record-Union (Sacramento, California), February 26, 1892, page 1.

But he didn’t stay away for long; and hadn’t gone very far:

The Morning Call (San Francisco), September 2, 1891, page 3.

[i] SF Gate, December 17, 1962 (excerpted from, December 16, 2012, accessed May 22, 2016).
[ii] The San Francisco Call, September 5, 1910, page 8.
[iii] In “escapes,” I count escapes and escape attempts for which I could find contemporary accounts, in which the escapee was able to get off the island.  I did not count reports of escapes in which the would-be escapees were caught on the island or never got more than a few yards into the water.  There may be more, perhaps many more, “escapes” or attempts that I missed because they were not reported, or I have been unable to find the reports.
[iv] Although Alcatraz had housed prisoners since at least 1861, “[i]n 1868 the department commander, Maj. Gen. Henry W. Halleck, renewed the idea of Alcatraz serving as the place of confinement for all long-time military prisoners in the department [(Department of the Pacific)], which at that time included California, Nevada, Oregon and the territories of Arizona, Washington and Idaho.  Once again, no specific orders for this development have yet been unearthd.  It is known that the adjutant general of the army, Brig. Gen. Lorenzo Thomas, was interested at that time in establishing military prisons and companies of discipline around the country.  A letter by Engineer Mendell to the commanding officer of Alcatraz in June 1868, indicates that Mendell had been approached about the feasibility of erecting a wooden prison on top of the guardhouse.” Erwin Thompson, The Rock: A History of Alcatraz Island, 1847-1972 Historic Resource Study (this 600 page volume is available as a pdf file from a a link at the bottom of this National Park Service webpage.
[v] Red Bluff Daily News (Red Bluff, California), October 12, 1920.
[vi] Santa Cruz Evening News (Santa Cruz, California), April 19, 1929.
[vii] Madera Tribune (Madera, California), March 12, 1930.
[viii] Santa Cruz Evening News, June 30, 1930, page 1.
[ix] Red Bluff Daily News, March 30, 1921.
[x] Evening Star (Washington DC), January 6, 1902, page 1.
[xi] The Coeur d’Alene Press (Coeur d’Alene, Idaho), March 7, 1903, page 4.
[xii] Los Angeles Herald, November 18 1918, page 1.
[xiii] The San Francisco Call, August 19, 1898, page 16.
[xiv] The Morning Call (San Francisco), May 6, 1890, page 4. The contemporaneous account of the escape says the prisoners were named Stone and Miller; but two later accounts of the same incident, say that Bennet, who escaped again two years later, was one of the escapees.
[xv] The Record-Union (Sacramento), February 26, 1892, page 1.


  1. Can I ask where did you get the picture and history on my great grandfather Leonard Wilmore aka Roger James of Hawaii? My grandmother Jeanette James was his 4th child with my great grandmother Anne Markiewith.

    1. The image is from his article, “The Convict’s Story,” published in, Wide World Magazine, Volume 18, Number 104, November 1906, page 169.

    2. Thank you. Can I ask where you got the info about him. some fact about his life are wrong. He was born in Kentucky. His father James Palmer who was Leonard's father was the son of Dr. George Wilmore and a Eliza Palmer was a slave. Leonard's mother was a half cast like his father. Later James Palmer married a woman named Cassie White who was Black and Indian and had other children. James could not have his white fathers name due to the doctors white family and was give his step fathers name of Palmer. As a big F**k You to his father he named his first born son with the Wilmore name. They are all from kentucky. There is another Wilmore family in Pennsylvania but they are of no relation. Leonard aka Roger had 2 children with 2 hawaiian women and my great grandmother Anna was a maid in his first wife's house. She is 32 years younger than he is but they had 8 children together and he had 1 child with her sister. Might of been the reason she divorced him. But that child by the sister is Bill Clark and wrote a book from my grandfather memoirs. Bill did not know that Roger James was his father and died when he was young. Bill was only told after his mother passed. I don't know why but I know thing about my grandfather that I was never told but knew about him anyway and was confirmed later. I don't understand it all. I am proud of who my great grandfather was and knew he did what he did was out of survival and not out of hatred otherwise he would of never married and had 8 children with a woman who's parents were from Poland and was white as you can get. Thank you for that pic I look at it every morning and know I have to honor and look up to him.

    3. I took several of the biographical details from Leonard's own story as published in Wide World Magazine.

  2. Ralph Roe and Theodore Cole supposedly escaped December 16, 1937,alcatraz. post cards were sent to the warden were in S. America.
    Supposedly the post card read : "Gone Fishing ".
    Frank Morris , John Anglin , Clarence Anglin escaped Alcatraz.6-11-1962.
    Supposedly John Anglin called a attorney for help in his sentences?
    Post card was sent to Clarence ChocktawKid Carnes.
    Christmas Cards were sent to Rachel Anglin boys mother.
    Cards had no Envelope but put in Post office box front house?
    Flowers were sent to Rachel Anglin from boys mother.
    Disguised Women were at Rachel Anglin funeral 73 with anglin family disguised
    in sun glasses that day as were picture taken with disguisedgals.
    Marie Anglin Widner claim brother G.R.Anglin had always contact
    with J.W.Anglin and Clarence Anglin 1962 to his death in florida.
    Fred Brizzi visit1992 Marie Anglin Widner told about 1975 picture Brazil.
    IF Anglin went to Brazil how come they were Rachel Anglin Funeral 1973?
    In the 1950s the Anglin Boys came and went on vacation in Mexico?
    The Anglin boys stole from stores, businesses and Bank 1958 ?
    While Fred Brizzi talk the Anglins record him secretly without his knowledge.
    Marie Anglin Widner and sons Dav /Ken went public with theories 2012.
    History channel made documentary Anglin escape in 2015 or so?
    Dave Widner wrote a book not so long after the show aired?
    Dave Ken 's : Anglin Museum brag about Whitely letter to them.
    Which Whitey Bulger brags that he helped john/Clarence escape rock?
    Alcatraz James Bulger transfer as serious escape risk inmate iq113?
    John Anglin supposedly written letter to _ ask for deal then he come in?
    John Anglin wrote Clarence died 2011 and Frank Morris in 2008?
    that they were buried under alias - unknown -anonymous names ?
    Maybe someone should check Ruskin cemetery /widner cemetery?
    Clarence Anglin was living, placing it in a rural area near Greenwood.
    Clarence Anglin and Frank Lee Morris previous history in Jackson County.
    clarence Anglin 7-6-45 florida industrial school Marianna fla mother got him out.
    anglin and Morris both had been in the Dozier School for Boys.
    A woman in the area Greenwood describe farm they were live at ?
    But when woman and authorities got there the place was vacated?
    (read/ read the information for yourself?)Two Egg is a real place. Located amidst the farms, woods and lakes of Jackson County, Florida.
    Two Egg Fla is near Marianna Florida that Clarence spent time at ?
    Highways Via I-10 E, I-75 S Ruskin Fla to Two Egg Florida border ala/Ga.
    Do you think authorities took letter seriously man that didn't serve his sentence?
    aging man was ask for a deal for medical help make tax payers pay for it ?
    If the Medical Help didn't heal man then Anglin family sue-blame the Systems ?

  3. Well I don't know why he thought he was native american indian but my great aunt Betty, who is Leonard's 10th child and myself both of our DNA shows we're not Indian. I saw that he wrote American Indian on my grandmother's birth certificate. This was a big surprise to all of us in the family after being told we are Indian our whole life.I have even contacted Patty Palmer's(Leonard's half sister)family as well to confirm the history as well. He may have gotten Cassie White and Sarah Moppin's history confused. Other than Leonard's mother writing the war department after Leonard's escape very little is known about her since he was raised by his father and step mother Cassie White.I tried to find the article you referred to but haven't found it yet but I am reaching out to my Uncle Bill Clark who wrote the book "To Live Another Day" based from Leonards memoirs. I am ordering his court record here in Hawaii and Court Martial records and military records. The records from the military related to Alcatraz were for unknown reasons were destroyed. If and when I get these records I will gladly send or post those records. There is even a story that Queen Liliuokalani had something to do with why Leonard was not returned to the military. Hope to clear this history up. Thank you and Aloha Jamie Holland Brown

  4. clarence Anglin 7-6-1945 MariannaFla Dozier School boys(rumor that Frank Morris spent time there as well?Woman claim clarence told her his story,TwoEgg/GreenWood fla but authorities got there men were gone? (read 2eggblogspot)Anglin's Childhood budy Fred Brizzi 1970s dealed in illegal deals to from outside U.S. Him have a airplane/yacht? He could come n go undeteched?Could Fred Brizzi take picture of John and Clarence Us(1970s)? And then have the Film developed somewhere outside Us Brazil ? If Marie Anglin Widner & anglin family had picture taken at Rachel funeral 1973(ruskin Fla) it must of been a special event to have 2 disguised males disguised as females then others have sunglasses on to hide their eyes?Then Have Christmas Cards with no Envelope drop in mail box not by postman but anonymous person ? Then have flowers given Rachel mothersday -with no receipt from flowerShop with price-name info? Then have the John/Clarence Picture with redclaydirt anthill -their is soil like that in Tn ,ala,georgia-fla etc?FireAnts ? Why did Widners come out 2012-benefit /gain -AnglinAlcatraz story?SanFrancisco John Anglin Letter2013 claim that Clarence died2011 and Frank Morris died 2008 ?Someone Needs go Ruskin Fla Cemetery check during those years ?Because If Anglins had contact AlcatrazEscapeBoys probarbly always had put in unmark graves (cremated?)