Alaskan Jail Break


Steven Levi

It was 6:30 on the morning of July 4, 1905. Roberts, a new guard at the federal prison on McNeil Island, southwest of Tacoma, Washington, was making his morning round when he made a disturbing discovery. While he had been on duty that night, keeping an eye on the desperados under his care, eight of them had vanished.

Examining their cells he discovered something even more embarrassing. The eight escapees had gained their freedom by tunneling through six brick walls and two ceilings. One of the ceilings was composed of sheet steel. How the eight convicts had been able to complete the work without being heard was a matter Warden O.P. Halligan, United States Marshal Hopkins and a host of news reporters were going to be asking for days.

Immediately after the alarm was sounded, Warden Halligan did a quick nose count. He was missing eight men, confirmed by their empty cells. Seven of the escapees were run-of-the-mill convicts,

Clyde C. Castle, from Tacoma, who had been sentenced to two years for altering money orders, with his term to expire on October 27, 1905.

James Leslie, from Alaska, who had been sentenced for larceny with his term to expire on August 18, 1905.

Joseph H. Malone of Fort Gibbon, Alaska, who had been sentenced to six years for rape with his term to end on December 4, 1908.

W. D. McCarthy of Tanana, Alaska, who had been sentenced to ten years for robbery with his term to expire on April 14, 1910.

Matt Moor, one of two Japanese escapees, was from Alaska and had been sentenced to five years for stabbing. His imprisonment was to end on May 16, 1908.

Edward Stickney, from Tacoma, had been sentenced to three years for counterfeiting with his term to end on July 5, 1907.

K. Takenouchi, from Alaska, the second of the Japanese escapees, had been sentenced to 20 years for manslaughter. His term was to expire on May 16, 1918.

The eighth man, however, could hardly have been called run-of-the-mill. He was the one prisoner the Warden could have guessed would be in the escape party even before looking over the log book. That convict was George Wade. A master escape artist, Wade had already been in — and escaped out of — McNeil Island at least twice and had slipped from custody twice more at another penal institution. A seasoned escape artist and long-time drug smuggler who knew the United States/Canada border area like the back of his hand, he was going to be a hard convict to catch.

The only real surprise for the Warden was the escape of Castle and Leslie. Both men had short sentences and were due to be released fairly soon, Leslie within a matter of weeks. Their escape did not make any sense. But then again, this was McNeil Island and a lot of things that happened on this island didn’t make sense.

Originally McNeil Island, located in the chilly waters of Carr Inlet, had been established as a prison site primarily to put as much distance as reasonably possible between the federal convicts and the population of Tacoma. The fact that this distance was primarily composed of the frigid salt water of the southern extremities of Puget Sound which could not be traversed without a boat made the site of the prison ideal. It

was close enough to Tacoma to be serviced by the businesses therein, but far enough from the city to allow the residents to breathe easily whenever the subject of murderers, bootleggers, and larcenous individuals was brought up.

On the island the prison itself was a collection of buildings which housed the cells, wire fences, and watchtowers. Escape was deemed unlikely because a prisoner would not only have to break out of his cell and compound area, but would have to leap over wires and skirt watchtowers before he made it to the shoreline. Then he would need a boat to make it to the mainland.

Inside the walls, McNeil Island was a melting pot of America’s criminal element. Men ranging from illegal immigrants about to be deported to murderers serving life sentences mingled with rapists, forgers, stabbers, burglars, and even a few reindeer rustlers. These men were the dregs of the courts of Pacific Northwest and Alaska.

As each man entered the institution, he was logged in with his height, weight, eye color, as well as his religion — sometimes listed as “heathen” — and his property, if he had any. It was a melting pot of nationalities and criminals. Prison life was intolerable with all of the charges that could be made of an institution of those days. The cells were sweltering in the summer and freezing in the winter. The food was substandard, medical care was lamentable and sanitary conditions medieval.

Though security was tight, McNeil Island was not escape-proof. It opened for prisoners in 1887 and there had been more than a handful of escapes by 1905. Some of them were even successful. One of the first was Leo St. Cloud who was serving a 40 day sentence for sending obscene material through the mail. He arrived on September 10, 1892, and slipped out of custody 22 days later. He was never recaptured. There were several other escapes over the next decade — including two by Wade — but none quite like the mass exodus of eight prisoners on July 4, 1905.

Of all of the escapees, George Wade was clearly the most notorious. Under the alias of “Charles Smith,” with his real name listed as “George Bates,” he had begun his penal career by being convicted of smuggling opium into the United States in December of 1891. He was found guilty by a Port Townsend court and sentenced to a year at McNeil Island. But he didn’t stay long. On March 11, 1892, he slipped out of custody and spent 11 days on the run. Recaptured, he made up for his escape, stated court documents, by working “extra hours every day” and was released on November 30, 1892.

Within two years he was convicted of smuggling opium again, this time under his true name, George Wade. While in 1891 he had been sentenced for smuggling about 15 pounds of the substance in 1894, a Tacoma court found him guilty of possessing “two trunks containing about one hundred pounds” of the drug. He was sentenced to McNeil Island again on July 17, 1894. Though he was supposed to serve two years at hard labor, he didn’t stay at McNeil Island nearly that long. A little more than two months later, on September 27, he escaped again. He and another prisoner were taking garbage outside the prison walls when both men made a “sudden dive for the brush” and disappeared.

Several days later, while guards were still out looking for Wade and his companion, two other prisoners poisoned the Warden and were able to escape as well. The Warden survived his bout with death and within a matter of days, three of the four escapees were re-captured. But Wade eluded the bloodhounds and disappeared.

For seven years Wade was able to evade the law. Then in 1901 he was arrested again. But true to his calling, he was able to escape. He gained his freedom before he went to trial only to be recaptured. Sentenced to a year in jail, he escaped before the end of his term but was recaptured and forced to finish his sentence. (There is no record of what the sentence for this transgression of the law might have been or where he was incarcerated.)

Three years later he ran afoul of the law again, this time in Nome, Alaska. He was sentenced to McNeil Island for the third time, in September of 1904, for larceny. But on July 4, 1905, he was once again on the lam.

The Escape

The drama of the eight-man breakout was just as fantastic as Wade’s record. McCarthy, Stickney, Wade and Malone were secured on the second floor of the prison while the other four men were in the cells immediately above them on the third floor. The men on the second floor, each from his own cell, tunneled into his neighbor’s cell and then into Wade’s cell. Now, with their combined manpower, they bored through the ceiling of Wade’s cell into Leslie’s cell immediately above them.

At the same time, the four men on the third floor were separately tunneling through the brick walls dividing their cells. When all prisoners met in Leslie’s cell on the night of July 3, their combined efforts allowed them to penetrate the sheet steel plates of the roof. Up through the gap, they ran across the roof of the prison and then slid down to ground level using a rope they had made of their blankets, stripped and braided.

What initially surprised the Warden was the time it took for the men to break out. The prison had allegedly been thoroughly inspected on Saturday, July 1, so it was assumed that all of the digging had to be have been done during the day on Sunday, Monday and Tuesday when the noise of prison routine hid the sounds of metal against brick wall. But how the eight could have escaped without being heard on the night of July 4 was a complete mystery — at least until the first escapee was caught.

Once outside the prison building, the eight men made a wide tour of the island to avoid the watchtower. Arriving at the boathouse, they forced the door and disabled the prison launch by removing a part of the boat’s engine and dropping it into the inlet. Then they stole two rowboats from the shed along with eight oars and disappeared into the gloom.

Once the escape had been discovered, the most important question for the Warden to ask was “In which direction will the escapees head — would they go south toward Oregon or head north toward British Columbia?” Going south was an option but not a good one. Six of the eight men were from Alaska and the other two knew the immediate area fairly well having lived there. Further, George Wade had made a living smuggling opium across the Washington/Canada border. The Warden gambled that the boats would head north.

There was another good reason for the men to run north. While any run to the south would lead them to populated areas, all along the route to the north were hundreds of miles of thickly wooded shorelines where men in boats could hide out during the day. Traveling only at night, the convicts could reasonably make Canada before American authorities could catch up to them.

The route that the escapees took was guaranteed to make it as difficult as possible for Marshal and his men to follow. Once in the boats, the convicts would have to pass Fox Island, go through The Narrows and then row into Colvos Passage between Vashon Island and Olalla before coast-hopping along Puget Sound until they reached the Canadian border. But even knowing the exact route was not going to make it any easier for the Marshal. Time was to prove this statement correct.

Assuming that the men would have to hide out during daylight hours, United States Marshal Hopkins ordered the outskirts of Tacoma were carefully monitored. Bands of law enforcement personnel reconnoitered the countryside looking for suspicious characters wearing clothing made of prison blankets and investigating reports of chicken stealing and other crimes that indicated a convict was possibly in the area.

Even with search parties beating the bushes as far north as Vashon Island, Marshal Hopkins was hard-pressed to keep track of the rumors. As more and more sightings were confirmed, Hopkins was able to develop a clear picture of where the prisoners probably were. To the best of his deductive thinking, one escapee had made it as far north as Olalla. Assuming that Wade would be the most likely candidate to have made it the farthest, Hopkins tagged this unknown escapee as Wade. If Wade were on his own, this meant that the prisoners had separated. This was good news for law enforcement because it meant that the remaining men could not collectively use Wade’s genius for escape. But, on the other hand, it was bad news when it came to capturing Wade because he was so unbelievably resourceful.

Hopkins further assumed that four of the men were on Vashon Island. At least one was in the vicinity of Defiance Point Park near Tacoma because a man matching the description of Matt Moor had been seen buying a fish. This probably also meant that Takenouchi was in the vicinity as well because, in the words of the newspapers, “the ties of racial consanguinity [were] looked upon by the searchers to keep the two Japanese together during the extremities of the pursuit.” But Hopkins could not account for the remaining prisoner.

It did not take long before Hopkins could place that man. At around 10 pm on Friday, two days after the breakout, Ed Stickney became the first convict to be re-captured. Apprehended in Point Defiance Park where Moor and Takenouchi had been spotted, Stickney had been boldly walking up to a trolley that would take him into Tacoma when he was recognized by Deputy Marshal Tom Morris. The convict was taken without a struggle.

“Hello, Ed,” Morris said as Stickney walked by the posse as if nothing was out of the ordinary.

“Well, you’ve got me, Boys,” was all Stickney replied.

Almost pleased at being re-captured, Stickney warmed up quickly. After a hot meal he was in a “good-humored and even playful mood,” the newspapers reported, and talked freely about how the escape had been affected. The men had been digging for months, he confirmed, using iron spoon handles to pry the mortar free from around the bricks. This confession tore the guts out of the Warden’s claim that all the digging had to have been done since the previous Saturday. It was also quite embarrassing for prison officials since the thorough inspection conducted the previous Saturday was supposed to uncover tunnels exactly like the six the prisoners has succeeded in digging.

By the time of Stickney’s capture, scraps of information were flooding in from all across the search front. One of the stolen boats had been recovered on Vashon Island and four of the convicts had been seen several times foraging for food on the island. But that information had not been without cost. Two posses had come upon one another unexpectedly and one group began firing before they had identified their targets. Ritter Wilkeson from Tacoma went down with a painful but not serious flesh wound in his right arm.

The posses were also using a new tool in hunting for the prisoners: photographs. McNeil Island had only started taking photos of the prisoners for identification since 1902. Now that precaution was going to become a tool of identifying the escapees. For the first time in Washington history, McNeil Island escapees would have their pictures in the paper — every paper — thus aiding the forces of law and order. Photos of the eight men were reproduced from the prison log and widely distributed to the searchers.

It was not until the next day that Leslie and Malone were captured. Malone was cornered on Vashon Island while Leslie was arrested as he walked into Kent. A bit of levity was added to the somberness of the search when Leslie released a copy of an epistle which the eight escapees had left for Halligan on McNeil Island. It read

Dearest Happy Hooligan,

We, the undersigned, feel very happy to bid you good-bye but have just received a letter from King Edward VII, so must tear ourselves away. But do not be concerned as to our welfare and do not be concerned as to the fact of our being hungry.

The bill of fare for a while will largely consist of light summer air and mountain scenery, but liberty sauce makes good eating.

Would not leave you, but for the fact that we might fall sick here in the penitentiary and die, as in the case of Poor Richards. [sic.]

Give our cordial regards to the rest of the farmers who pass themselves off for guards and assure them of our lasting gratitude for their stupidity.

While we are admitting that we may be brought back to your hash resort at any time, we think such an event highly improbable.

We cheerfully admit that the steel plates were a tough proposition, but you know the old saw, “Where there’s a will there’s a way.” Yours in derision.


The fourth man to be taken was Matt Moor. Wearing a “black, slouch hat, common jumper and black pants with patches,” the press reported, he was apprehended in a railyard near Ravensdale with a “sack of berries and a sack of herbs and a cabbage” Moor had crossed over from Vashon Island to the mainland in a small rowboat with Leslie and McCarthy in broad daylight. Takenouchi apparently swam the channel and came quite close to drowning. After he recovered from his swim, he walked into a logging camp about two miles from Olalla where he fell into a deep slumber. He awoke in chains on Wednesday, July 12th.

On the same day, W. D. McCarthy was apprehended outside Ellensburg. A posse came upon a gang of men and while one deputy was talking to a group of them, McCarthy made a break for the forest. The sheriff ran after the fleeing convict, yelling for him to stop at least six times. When McCarthy refused to halt, and appeared to be getting away, the sheriff shot McCarthy in the upper leg. McCarthy made another 20 yards before he collapsed. The wound was not fatal.

The next Friday, ten days after their escape, Malone, Leslie, Moor, Takenouchi, Castle and Stickney were back in McNeil Island and “immediately placed in chains.” While they may not have been thrilled to be back in custody, they must have taken some pleasure in watching teams of 30 men work at repairing the brick walls through which they had so painstakingly dug. It was take almost a month for the prison to repair the holes in the brick walls and ceilings. The troupe of seven was as complete as was it ever going to be on August 9, 1905, when the wounded McCarthy was transported back to McNeil Island.

But George Wade never returned.

Clyde C. Castle’s sentence was extended to March 24, 1906. He was finally released on March 29, 1906.

Joseph H. Malone was discharged on March 6, 1909. He returned to Alaska where he was subsequently convicted of rape, the same charge for which he had been convicted the first time, under the name Herbert Flemming. He was sentenced to 8 months at McNeil Island and, upon his release, was supplied transportation to Cleveland, Ohio.

After his recovery from the rifle bullet, William D. McCarthy was relocated in Leavenworth, Kansas, on October 6, 1906. Over the next seven years he was transferred twice to the Government Hospital for the Insane in Washington. Through some manipulation of the prison rules, he was denied all of his Good Time, i.e., that time off his sentence which he had earned for being a model prisoner, even that which he earned after the escape attempt. This caused him to be sullen and morose and a growing danger to those around him. He eventually wrote to legendary Alaskan judge James Wickersham, the man who had sentenced him in the first place, asking for assistance in being released. Wickersham interceded on his behalf and McCarthy was let out of prison in July of 1912. Though McCarthy may not have known it, he might have had fate on his side. James Wickersham’s brother, George, was the Attorney General for the State of Washington, and the man who ordered McCarthy released.

Matt Moor was released December 7, 1908, while K. Takenouchi, was transferred to Leavenworth on October 6, 1906, — the same day as W. D. McCarthy. No record remains of Takenouchi’s time in Leavenworth or what become of him after his release.

But there are quite a few records regarding the fate of Edward Stickney. In the McNeil Island logbook, his original release date of July 8, 1907, is scratched out with two other notations added. One reads “7–10–07” and the other “March 24, 1908.” After his return to prison Stickney flooded the court with paperwork. Over the next two years his case generated over 800 pages of correspondence relating to his request for an early release. These records still reside in the National Archives in Washington D. C. The appeals must have worked as Stickney was discharged from McNeil Island on October 17, 1907.

Finally there is the matter of what happened to George Wade, ring leader and master escape artist. After his escape from McNeil Island in 1905, he disappeared from the documents of the Pacific Northwest. Assuming that he continued his life of crime, the United States Bureau of Prisons was contacted in 1992. Had a George Wade been incarcerated anywhere else in the prison system? Yes, it replied. A George Wade spent time in Leavenworth from July 5, 1927, to February 10, 1929, for violation of the drug act. This could be the same man.

As George Wade had continued to list his home of record as Burlington, Vermont, the Public Record Division of the State of Vermont was contacted for a birth certificate. This document revealed that George Franklin Wade had been born on October 27, 1858, to Jane Bradley and Luther Wade of Manchester, Vermont. On the off chance that George had returned to his home after age made his encounters with the law less desirable, the Office of Vital Statistics was asked if a death certificate for a George Wade was also registered.

Surprisingly, there was one. But was it the same man? A 90-year old George Wade died in Manchester on September 4, 1948. Though his obituary in the Manchester Journal indicated that Wade had been a “life-long resident,” his death certificate stated that he had only been in the community for “18 days.” The deceased was born on October 27, 1857 — the same month and day as the original George Wade, but the year was one digit off. The father’s name for both men was the same, Luther, but the mother’s name was different. The death certificate lists the woman’s name as “Mary Ellen Brown.”

Were these two men one and the same? Did the legendary opium smuggler and master escape artist return to his roots in Vermont? No one will ever know for sure, but the legend of George Franklin Wade is still alive today, more than a century after he broke out of his first prison in March of 1892.

Steve Levi has more than 80 books in print or on Kindle. He specializes in books on the Alaska Gold Rush and impossible crimes. An impossible crime is one in which the detective has to solve HOW the crime was committed before he can go after the perpetrators. In the MATTER OF THE DESERTED AIRLINER, an airplane with no pilot, crew or passengers lands at Anchorage International Airport. As the authorities are pondering the circumstances of the arrival, a ransom demand is made for $25 million in diamonds and precious stones. Chief of Detectives for the Sandersonville, North Carolina, Police Department, Captain Heinz Noonan, is visiting his in-laws in Anchorage when he is called onto the case. For the next 36 hours, he pieces together the puzzle of how the crime was committed. But can he solve the crime, free the hostages and locate the perpetrators before the ransom is paid? h




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Steven C. Levi

Steven C. Levi

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