Santa Cruz County History - Crime & Public Safety

Anthony Azoff and the Murder of Detective Len Harris
by Phil Reader

Being an account of the attempted robbery of the Wells-Fargo Express Office in Boulder Creek, and the subsequent killing of Southern Pacific Detective Len Harris.


The last two decades of the l9th century were years when the phrase "train robbery" became catch words for the people of California. It stirred them up and captured their imagination. The much hated Southern Pacific Railroad was at the height of its power, stretching its tentacles up and down the state. The company's land grabbing schemes were alienating large segments of the population and, as a result many small farmers found themselves dispossessed.

A few of these embittered farmers and laborers turned to crime and Southern Pacific trains and depots became prime targets for masked desperados. The Dalton Gang, Sontag and Evans, and the Johnson Boys found their names splashed across the pages of California's newspapers. They found safe refuge in the homes of sympathetic farmers. The area around Visalia quickly became a hot bed of such activities.

Santa Cruz County was not without its contributions to this jaded saga. Daniel (Three-fingered Jack) McCall, son of pioneer Hugh Pablo McCall, made history by becoming the first native Californian to be killed during an attempted train robbery.

McCall, a wood chopper by trade, had left Santa Cruz in 1892 and traveled up and down the state before settling in Visalia in 1894. He fell under the spell of Si Lovern, a barkeeper and old associate of Chris Evans and the Sontag Brothers. It was at Lovern's saloon that McCall, Lovern, and Obie Britt, a former Soquel resident, hatched the plan to rob a Southern Pacific train.

The robbery took place on March 19, 1896 when Dan McCall crawled aboard a train #19 as it pulled out of Goshen on the way to Visalia. At the Targus switch he climbed across the train intending to force the engineer to stop the locomotive at a deserted siding, where the other gang members would rob the express car.

But what McCall didn't know was that Britt had betrayed their plans to the Tulare County Sheriff and that two deputies, Earl Daggett and G. W. Reed, were waiting for him on the tender car. In the shoot-out that followed, Daggett and Reed were wounded and Dan McCall was killed outright. Si Lovern was later arrested and given a life sentence in San Quentin.

But all of this came, however, two years after the most famous criminal event in the history of Santa Cruz area railroading.

The Shooting

The story of the killing of Len Harris actually began on Monday, May 14, 1894, when Harris and fellow Southern Pacific Detective William Kelly arrived at the office of Santa Cruz County Sheriff Jesse Cope. The detective explained to Cope that they had uncovered a plot to rob the Wells Fargo Express office at the railroad depot in Boulder Creek. One of the plotters, George Sprague, had come forward and informed the company that Anthony Azoff and another man were planning to hold up the expressman on the night of the 15th.

Since Azoff, a former Boulder Creek resident, knew Sheriff Cope, it was decided that the sheriff should not take part in the action because his presence in the area might tip off the schemers. Cope was to remain close to the telegraph in case he was needed later.

The following afternoon Harris, Kelly and Constable Isaiah Hartman secreted themselves inside a box-car which had been placed in front of the depot. All three were heavily armed and Wells Fargo express agent William Gass had been forewarned of the possible robbery.

At about 8 o'clock that evening three masked men approached the depot from the north. They were Azoff, the informant Sprague, and another man unknown to anybody but the gang leader. The latter two remained on the depot platform while Azoff continued on into the office.

As he stepped through the door he pulled a fearsome looking 44-caliber pistol out from under his cloth coat. The robber ordered Agent Gass to open the safe and at the same time handed him a sack in which to place the money.

Before the agent could comply, the three peace officers jumped put of the box-car with their weapons at the ready. Kelly and Hartman turned their attention to the two bandits on the platform, while Harris went in after Azoff.

"You'd better surrender." He shouted, "I've got the drop on you."

But Azoff remained calm and collected. Hardly changing his position he turned his pistol back under his arm and instantaneously fired two shots before making any move which may have excited or alarmed Harris. Both bullets tore into the detective's mid-section and he fell forward groaning that he had been hit.

Out on the depot platform, Kelly and Hartman had opened fire on the two remaining outlaws. For some unknown reason they had not been told that Sprague was an informant. So while bullets were flying all around him he threw up his hands pleading with them to hold their fire, screaming that he was on the officers side. Meanwhile the third desperado made his getaway into the darkness.

After shooting Harris, Azoff bolted out the depot door, ran through the railroad yard heading in the direction of Bear Creek Road. Constable Hartman followed him for about a quarter mile blazing away with his shotgun. The fleeing robber returned the fire over his shoulder, squeezing off five shots before disappearing into the woods.

Hartman went back to the depot, made Harris as comfortable as possible, and then telegraphed Sheriff Cope in Santa Cruz. Cope and Deputy Wright set out for Boulder Creek where they were met up with Hartman, and the three men started out on the trail of the gunman.

Len Harris

Detective Harris was taken to the Morgan Hotel where he was tended to by Dr. Allen. The two bullets had passed through his abdomen tearing up some vital organs, so his wounds were pronounced as fatal.

The following morning railroad Superintendent J. A. Fillmore sent a special engine and car down to Boulder Creek to carry Detective Harris to his home in Oakland. Accompanying him on the journey were his son Jack Harris and Doctors Allen and Morgan. He arrived at his home in the late afternoon and at 11:30 that night he lapsed into a coma and died.

Leonard Harris was born in upstate New York in 1828. He moved to California during the gold rush and by 1856 he was working as a lawman in Sacramento, serving both as constable and sheriff. During the construction phase of the Southern Pacific Railroad he was hired as a special detective and for many years he was chief of the detective division.

Harris was always known as a brave and clever lawman. One of his best pieces of work happened while he was stationed in the Arizona Territory. The overland train was held up at Pantano, Pima County, and the treasure box and mail bags were stolen. Harris and a band of Indian trackers followed the robbers into a lava bed where the trail was lost. He found a place where the thieves had last camped. Among the ashes of their fire he found pieces of a charred newspaper which had been published in Oregon. With this slender lead he discovered that two men, a saloon keeper in Silver City and a store keeper in Benson, were subscribers to the paper. The rest of the evidence was easily obtained, and a tough named Gambler Bob was included in the gang that eventually got long terms in the Yuma Territorial Prison. In 1888 he pursued a gang that had committed a robbery on the Sonora Road in Arizona. He and Marshal Bob Paul were in charge of the posse, and Harris was always in the lead. The criminals had gone into the Sierra Madre Mountains in the middle of a blinding snow storm. Besides the bad weather, there was always the chance of meeting Apache Indians. They finally came upon the bandits beyond Chicuahua and a pitch battle ended in the death of the four highwaymen.

One day in Tucson, Detective Harris won the admiration of a trainload of tourists when he disarmed a drunken cowboy who was intimidating the passengers. He simply pulled the rifle out of the cowboy's hands and cursed him for being a fool, after which he turned him over to the local sheriff.

At Alila, in the San Joaquin Valley, on September 4, 1891, he was on a train which was held up by the Sontag and Evans Gang. He had started to repulse the robbers when he received a wound in the back of the neck. He was never able to fully recover as the doctors were unable to locate the bullet. As a result Harris' right arm was to remain partially paralyzed.

Just prior to being called to Santa Cruz, Harris was investigating a robbery in Los Angeles.

So this was the type of brave and courageous man who was buried on May 20th, 1894. Len Harris was a veteran of the Mexican War and one of the greatest lawmen in the history of the old west. He left a widow and two children.

The Pursuit and Capture

On the night of the attempted robbery at Boulder Creek, Anthony Azoff was last seen going into the woods at Bear Creek Road. Sheriff Jesse Cope at the head of a posse had followed him, rummaging around in the darkness for about an hour in a vain effort to locate the killer. They returned to Boulder Creek and wired the sheriffs in surrounding counties requesting their help and including a description of Azoff.

By daybreak the next morning there were three posses in the saddle scouring the Santa Cruz Mountains. Sheriff Cope divided his men into two groups. One went over the hills toward Saratoga, while the other group searched Bear Creek Road and other roads which led over the mountains.

Sheriff Bollinger of Santa Clara County started out in a westward direction from San Jose, while San Mateo deputies secured the roads leading into that county. The lawmen had two fears. One was that Azoff would find his way to the coast and follow the beaches up to San Francisco, where he might board an out-going vessel. Another possibility was that he could hide in the rugged Big Basin region for as long as he wished. The bandit had worked cutting lumber in the mountains and knew the area well. He had many friends among the Russian and Finnish lumbermen who would supply him with food and information.

The Southern Pacific Company offered a $500 reward for his capture hoping that the money would serve as an inducement to one of Azoff's acquaintances to turn on him. Over the next few days the fugitive was reported as being seen in Los Gatos and in the vicinity of Saratoga. All leads proved to be futile.

Two men found Azoff's coat in the Boulder Creek train yard. In a pocket was found a note which read: "Ask and you will receive. Keep my uniform till I return." What that meant no one was able to learn, for the bandit showed no sign of returning.

Then a mysterious fact was uncovered. On Monday, the 14th, when detectives Harris and Kelly had arrived at Boulder Creek they registered under fictitious names, and soon afterwards someone wrote the words "man hunters" after their signatures. When Harris returned to the hotel after dinner, he saw it and asked who did it. No one could tell him, so he erased it and left the hotel. When he came back later the word" hunter " was again written under his name. Once more he questioned the hotel employees, but still no one knew who had written the words.

A still more mysterious occurrence took place in Boulder Creek on the evening of the Saturday, the l9th. For several nights a stranger had been seen making purchases in town and then disappearing in the direction of the San Lorenzo River. Once he went into a drug store, saying he wanted some medicine for a wound, as his hand had been cut.

Ben Mashall was asked to keep an eye on the stranger, who was suspected of bringing food to Azoff. On Saturday night, Marshall was waiting for the suspect to make his appearance in town. He saw the stranger about seventy-five yards away when suddenly, without warning, the man pulled a pistol and began shooting at Marshall. The lookout returned the fire, each man getting off four shots. The gun play was heard in Boulder Creek and Sheriff Cope hurried to the scene. But no trace of the stranger would ever be found. He had mysteriously disappeared. Most believed that he was the third bandit who had escaped during the depot shoot-out.

While this was taking place a farmer named J. Schroeder was riding through his wheat fields near Redwood City when a man answering Azoff's description approached him and asked for work. He directed the man to his ranch saying that he would be there soon. Instead he went directly into town to tell an officer. The man (later identified as Azoff) waited around for a short time and then started off down the road to San Jose. A little further on he encountered another man who recognized him, and this man also reported him to the sheriff.

Under Sheriff J. H. Mansfield, accompanied by Deputy Jonathan Butts in a buggy, took to the road that runs between Palo Alto and Mayfield. There were many tramps on the road and they were each checked for their identity. By then it was dark and the lawmen carried a lantern.

At last about six miles from Redwood City they encountered still another wanderer and pulled up, stopping on either side of him. Mansfield engaged the man in easy conversation while Butts checked him out closely in the light of the lantern. Following a prearranged signal both deputies pulled out their revolvers and pointed them at the murderer's head.

"Azoff," said Mansfield, "I want you!"

They quickly relieved him of his 44-pistol and fifty rounds of ammunition while securing him to the back of the buggy. Within an hour he was locked in a cell of the San Mateo County Jail and held under twenty-four hour guard.

Anthony Azoff

Photo of Anthony Azoff
Azoff's San Quentin "mug shot."

When arrested, Anthony Azoff, was a thirty-five year old man of Russian origin, who stood 5 foot 9 inches and weighed 160 pounds. He had a stocky build and wore a long droop mustache. His clothes were those of a common laborer and his bearing was erect and alert.

Over the next few days bits and pieces of his biography began to appear in the local press. He was born in 1862 somewhere in Virginia of Russian immigrant parents. Orphaned at an early age he began to drift around the country.

In the 1880s he worked as a cowboy in the plains states and settled for a few years in the Arizona Territory. During this time he ran with a wild crowd and he was implicated in the Prescott train robbery. But there was not enough proof to indict him and so he was released. He later crossed the border into Mexico and was jailed for a crime of a serious nature. Azoff and his cell mate managed to escape from prison and returned to the states.

1888 found him in Boulder Creek where he worked at Peery's Mill in the mountains for a time before being hired by James F. Cunningham in his mercantile business as the driver of a delivery wagon. When Cunningham sold out to Daugherty and Middleton, Azoff remained on the job. While driving the wagon he first met George Sprague. During this time he married and his wife gave birth to a daughter.

In 1891 Anthony Azoff and his family left Boulder Creek and moved to Eureka where they remained for a period of one year. At this time Azoff and his wife began to quarrel and she went to Oakland to live with her married sister. He followed her and they lived together off and on until April of 1894 when she moved back home to her parent's farm in Missouri.

About this time Azoff ran into George Sprague on a street in Oakland. They had not seen each other since the days when they had worked together in Boulder Creek. Azoff began to discuss the possibility of robbing the train or the railroad depot in Boulder Creek, as it was an area with which they were both familiar. He even suggested that they start calling each other Chris and John, in open admiration of Chris Evans and John Sontag - the Tulare County bandits.

Azoff bragged about his roll in the Prescott train robbery as well as an attempt to hold up a train near Sacramento. The more Azoff pressed him on the proposed Boulder Creek job, the more Sprague was determined to turn him in. On May 10th, he betrayed their plans to the Southern Pacific, who in turn sent Harris and Kelly out on their deadly mission.

The Trial And Execution

On May 21, there was a large crowd at the Santa Cruz depot who had gathered hoping to catch a glimpse of Anthony Azoff, the man killer. But they were disappointed because Sheriff Cope had alighted with his prisoner at the Seabright station where Under Sheriff Wright met them with a rig and hustled them to the jail by a back route.

That day he was positively identified by a number of people including Wells-Fargo Agent Gass, and J. F. Cunningham, his former employer. Afterwards he was photographed and taken before Justice Craghill for a preliminary hearing. Trial was set for June 25, in Superior Court and Frank Stone was appointed as his attorney.

Azoff's trial on the charge of murder was a mere formality. In his testimony George Sprague outlined the defendant's detailed plan for the robbery explaining his roll and that of the mysterious third outlaw. Afterwards Agent Gass identified Azoff as the man who had attempted to hold him up and had shot Detective Harris.

It took the jury forty-five minutes and only two ballots to find Anthony Azoff guilty of first degree murder. This sentence carried with it a mandatory death penalty. His date of execution was set for September 12, 1894. At the pronouncement of sentence Azoff remained defiant and indifferent, as he had through out his trial. He was taken to San Quentin and put on death row while his lawyer attempted an appeal.

Anthony Azoff Executed June 7, 1895.

While he was in prison a reporter from the San Francisco Chronicle was sent over to interview him. In his published article the reporter expressed amazement at the state of mind which Azoff retained in his death cell.

"Anthony Azoff isn't at all conventional." He wrote, "When he is amused his eyes twinkle, and he gives such a grin. ...He is positively cheerful, with a guilelessness that is quite childlike."

"You give the impression that you're rather delighted to be here."

"Now that's just it," Azoff responded, beaming at being so well understood."I'm getting the best of it. This is better then scraping for a living on the outside any day. Before I came here I had a dread of this place .... Instead, I have a fine room, dry and clean and white as snow. And such beds. It's almost worth hanging to have a nice, soft place to lie in. I like my room best in the evening. Then it seems so cozy and homelike. We light the lamp and read until 12 o'clock. Then we blow it out, though the prison officers haven't said we must."

Soon all of his appeals had been exhausted and a new date for execution was set for June 7, 1895. Anthony Azoff was to meet his death in the same resolute manner with which he had lived.

On the appointed day there were three men who were to be hanged. Azoff, Amelio Garcia, a murderer from Monterey County, and Patrick Collins, who had killed a bank teller during a robbery in San Francisco. The three condemned men were awakened at 7 o'clock and ate heartily of fruit, coffee, and bread. Afterwards Father Logan, a Catholic priest from San Rafael, arrived at the prison and offered consolation to the three men. At 8:30 the three men bathed and donned black trousers and dark shirts.

Meanwhile three rough wooden caskets were lined up beside the gallows, and a crowd of men, including Jack Harris, the son of Detective Harris, were let into the prison courtyard to witness the executions. First to hang was Amelio Garcia. He died "game " and his body was placed in the first of the caskets.

Next came Anthony Azoff. He mounted the steps to the gallows with a firm tread and looked confidently about him. The knot of the noose was adjusted around his neck and a black hood slipped over his head.

Just before the trap was sprung he said simply,"Good-bye, boys. Here goes a brave man."

He had died with an air of defiance and braggadocio, displaying the courage for which he had always been noted. Azoff's body was placed in another of the wooden coffins and later that day all three men were buried in unmarked graves at the prison cemetery.


For many years there was a trophy case which sat in the far corner of the Sheriff's Office at the county courthouse on Pacific Avenue in Santa Cruz. Prominently displayed in this case was the large, fearsome-looking, nickel-plated, 44-caliber pistol which had been used by Anthony Azoff to kill Detective Len Harris on May 15, 1894. What became of this pistol is unknown.

Copyright 1991 Phil Reader. Reproduced by permission of Phil Reader. Photograph courtesy of Phil Reader.

View similarly tagged articles:

criminals, murder, trials


It is our continuing goal to make available a selection of articles on various subjects and places in Santa Cruz County. Certain topics, however, have yet to be researched. In other cases, we were not granted permission to use articles. The content of the articles is the responsibility of the individual author. It is the Library's intent to provide accurate local history information. However, it is not possible for the Library to completely verify the accuracy of individual articles obtained from a variety of sources. If you believe that factual statements in a local history article are incorrect and can provide documentation, please contact the Webmaster.