The Bicycle Bandit and the Brother Who Loved Him

Part 2

Old Colony History Museum
5 min readMar 1, 2018

(If you missed Part I, you can find it here.)

On the morning of August 8, 1896, the Taunton police department sent five officers to arrest young Herbert Willis, suspected of being the “bicycle bandit” responsible for a number of robberies and assaults throughout southeastern Massachusetts and northern Rhode Island. After a search of his home turned up lots of stolen goods but no suspect, the policemen walked the short distance over to the Willis family’s fish market on Weir Street. When confronted there by the officers Herbert put up a vicious resistance during which two of the cops were injured. Fortunately the others were able to subdue the young man despite the two pistols he pulled from his pockets.

Once in custody Herbert talked freely about his adventures as the “bicycle bandit,” and his story led police to a cave near the bridge on Fisher Street in Taunton, where a large cache of stolen goods — including bicycles and several weapons — was discovered. The next day, after refusing to answer any questions about the murder of Fred Strange, Herbert suddenly confessed to that crime as well and gave police a full statement admitting his guilt. He also told police that he and Strange had known each other quite well and that he had attended the funeral of the friend he had murdered. On August 10, Willis was arraigned in Taunton District Court, where he waived examination and saw his case bound over for action by a grand jury. He was indicted in November.

Herbert’s trial, held in Taunton at the Bristol County Superior Courthouse on February 1, 1897, was anti-climatic. District Attorney Andrew J. Jennings, who five years before, as an attorney in private practice, had successfully defended Lizzie Borden, accepted a deal allowing Willis to plead guilty to second-degree murder in return for a life sentence. The 20-year old killer, spared from the possibility of death in the electric chair, was immediately transported to the state prison in Charlestown, Massachusetts.

While Herbert’s downfall shocked his neighbors, it devastated his family. Driven to distraction by his elder son’s disgrace, Samuel Willis simply walked away, abandoning his wife and six younger children. This placed the heaviest burden on 17-year old Everett, who worked long hours in a vain attempt to save the family’s fish business. Everett revered his older brother and was heartbroken at the thought that he would spend the rest of his life behind bars. Additionally, not knowing when — or if — his father would ever return placed a strain on the boy that was almost unbearable.

Charlestown State Prison with the Rotunda in the background. Photo from the Boston Public Library.

Visiting at Charlestown was limited to one hour on the first Tuesday of each month, and Everett attended faithfully. Seeing his brother in a maximum-security prison among hardened criminals was depressing, and Herbert didn’t help matters any by telling his younger brother that he would rather die than stay there. “I could think of nothing else, day or night,” Everett later said. Herbert “seemed to be wasting away . . . he could not remain there and live.”

After months of such painful visits, and in a decision that he would regret for the rest of his life, Everett agreed to help Herbert fight his way out of the prison. “I thought only of him,” Everett said later. “It seemed as if life was worth nothing to me, with him in prison.” The plan was set for Tuesday, August 10, 1897, and Everett spent the evening before the breakout shooting pool in Taunton. He was up the next morning in plenty of time to take the train to Boston, arriving well before the 10 A.M. start of visiting hours.

Under a hard-to-believe but soon-to-be-changed policy, the guards at Charlestown did not search visitors, and 17-year old Everett, with two fully loaded pistols in his pockets, was admitted to the rotunda of the prison, where he joined the waiting friends and families of other inmates. At exactly 10 A.M. Herbert was brought into the room and took a chair opposite his younger brother, within sight of two prison guards.

It would be an understatement to say that the escape plan was half-baked: At the end of the visitation period, as the brothers were about to say good-bye, Everett was to pass one of the guns to Herbert and the two would overpower the astonished guards and force their way out of building and onto the busy street, where they figured to disappear into the crowd.

That is exactly what did not happen. At the end of an hour of nervous small talk, a guard told the Willis brothers that their time was up. As they rose from their chairs, Everett quickly passed one of the revolvers to Herbert and kept the other for himself. “Hands up!” Herbert shouted as he leveled his pistol at the officer closest to him. Everett, who pointed his gun at the other guard, later said that the brothers were certain that the guards would offer no resistance. They were dead wrong because, although caught by surprise, both officers drew their own weapons and a fierce gunfight broke out amongst the women and children visiting with other inmates. One of the guards, a 73-year old veteran of forty years at the prison, was wounded in the arm and leg as the sound of gunfire brought the full complement of officers running toward the rotunda.

In an interview with the Boston Herald several weeks after the incident, Everett claimed to have deliberately fired over the heads of the officers in an effort to avoid injuring anyone. However, when prison officials reached the rotunda they saw both Willis brothers — their ammunition expended — attempting to bludgeon the guards with the butts of their pistols.

The first arriving officer fired several shots in the direction of the brothers, and his bullets found their mark. Herbert was hit four times, including twice in the head, and Everett was injured by two bullets, one of which left him with a dangerous head wound. It was later determined that more than 30 shots had been fired during the melee.

Herbert, gravely wounded, was taken to the prison infirmary, where he died three days later without having spoken a word. Everett was removed to the Massachusetts General Hospital and his recovery was in doubt for several hours after the shooting. Newspapers reported that on the way to the hospital, one of the attendants told the ambulance driver that he thought Everett had died, whereupon the injured boy opened his eyes and said, “Not by a long shot!” He survived, but that one youthful act of impulsive brutality would haunt him for the rest of his life.

Stay tuned for the third, and final, part of this story.

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Old Colony History Museum

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