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Eastview, Charles Southmayd's Berkshire cottage in Stockbridge, is still a private home today. But in 1893 it was the site of an incident involving The Gentleman Burglar. Photo courtesy Landvest

CONNECTIONS: The Gentleman Burglar, part 1

By Tuesday, Jan 23, 2018 Life In the Berkshires 1

The headline read: “Stockbridge Is Under Arms — Terrified by the Acts of a Mysterious Burglar.”

It was Sept. 10, 1893, and the New York Times was not mincing words. This, they wrote, was a “Reign of Terror,” no less.

Whoever the miscreant was, he had a taste for widows. In daylight, the thief entered the home of a Stockbridge widow and took $100. A few days later, he entered the home of the Widow Moore. It was night. He woke her and demanded money. In recounting her harrowing experience, she said, “He spoke in a suave and gentle tone.”

At that moment, a simple report took on the characteristics of enduring myth. From that day, he was known as “the Gentleman Burglar.”

Moore went on to describe him as “tall and well dressed with what appeared to be small soft hands, and a fine handkerchief covering his entire face.”

A newspaper clipping from 1893, after the Gentleman Burglar was caught.

Recalling her childhood, an elderly woman said, “I remember seeing a handkerchief. It was red with two holes in it for eyes. My mother told me it be­longed to a thief dubbed the Gentleman Burglar.”

The Times article dedicated a full page to the report: “The once quiet peaceful town now sleeps with barred doors. The watchmen in the street and the detective are on the alert for a tall man with arching eyebrows and a mesmerizing voice.”

With sobriquet established, the Gentleman Burglar changed his modus operandi. He entered Eastview [i], the Berkshire cottage of Charles F. Southmayd. He stood over Southmayd as he slept. It wakened him, and the burglar said, “Be very quiet and I won’t harm you.”

Just then, Miss Southmayd woke and called out from her room, “Charles, what is it?”

In an effort to protect his sister, Southmayd replied, “Nothing, go back to sleep.” Yet he was very disturbed by the incident.

Edith Wharton experienced a similar alarm at a hotel in Europe, and said, “Let no one ever speak to me of fear who has not awakened finding an intruder looming over her.”

After the home invasion, Southmayd refused to open Eastview, stopped coming to Stockbridge, and yet refused to sell it.  He confided to Choate that he hoped, when he died, it would burn to the ground. Southmayd died in 1911 and the house stands to this day.

In “Remembering,” Nathalie Sedgwick writes: “Alick read the no­tice of a reward in the post office: ‘$1,000 for apprehending the villain.’ Alick set a number of traps but the burglar omit­ted the Sedgwick house stealing jewels at all the other Stockbridge homes near around. Mrs. David Dudley Field had a hand-to-hand struggle with the same marauder…The burglar stole the jewels of an old maid opposite. The only man who had ever been in her bedroom, he melted her frozen libido. ‘He took everything away from me so quickly and gently, it was a pleasure.’ she testified.”

A Miss Stetson had a very thrilling experience according to the Times: “…at that instant a sight confronted her that drove every drop of blood in her body to her heart and paralyzed her with fright. Standing in the doorway was an apparition unearthly in its appearance; intensified in its ghostly outlines by the flickering lamp it held in its muffled hand. Six feet and over in height, looking taller and more spectral by the shadows heaving around it, a derby hat pulled far down over the forehead, a man’s hemstitched handkerchief drawn tightly over the lower part of the face and secured behind the ears, the figure before her could not have imbued her with more terror had she seen it come up out of the grave. In the right hand was a revolver; both feet were bandaged with towels….”

In relating the episode, Miss Stetson said: “The instant he spoke, the tension snapped and I was myself again. The voice was low, musical, soothing, and mesmeric in its effect. The change from the stifling silent presence to the talking human being was like the passing of a re­freshing summer breeze.”

Nonetheless, what the man said was “I want your money.”

Miss Stetson claimed she had none, and added, “I only came to stay the night with my friend because she is afraid of you.”

The Butler Swan cottage. Photo courtesy Austen Riggs Center, of which it is a part today.

Her friend was Mrs. Swan. The Gentleman Burglar crossed the hall and entered the bedroom of the lady of the house.

“I have a pistol,” Mrs. Swan exclaimed.

“So have I,” the burglar replied. He advanced toward her and demanded she give him her pistol. “You might hurt yourself with it.”

But the lady demurred, “I can’t give it to you, it is borrowed.”

“Very well,” he replied. “I will take it from you, because you might hurt yourself and I will leave it downstairs.”

He then walked over to her dressing case and picked up her rings.

“Won’t you please leave that one?” she cried, believing it was her emerald. “It belonged to my mother. I prize it highly.”

The thief nodded his head and replaced the ring on the silver tray. He took $80 from her purse, walked to her desk and asked, “Where is the key?”

“I don’t know. I have been thinking where I could have laid it. Your visit was so unexpected that I am unable to collect my thoughts.”

As he left Mrs. Swan’s bedroom, she added, “Don’t you think you might seek some other employment?”

Before leaving, he returned to Miss Stetson’s room and demanded her watch. She said she had none. He asked, “On your honor?” he said, raising his eyebrows.

The next morning, Mrs. Swan discovered he left the diamond ring he was holding and took the far more expensive emerald.

His next visit was to the home of Mrs. David Dudley Field. His face mask was now a piece of black silk. She tried to attack him. He lifted her up off the floor.

“You will get hurt,” he exclaimed as he tried to shake himself free, but she hung on in desperation, shrieking all the while. The noise awakened Mr. Field’s valet, who now rushed into the hall, pistol in hand.

“Shoot!” cried Mrs. Field to the astonished valet. “Don’t mind me! This man is a robber and he has my watch.”

The valet stood paralyzed. Then, with a keen sense of the proprieties but no sense of what was needed, the valet said, “I must get my wrapper,” and departed for that indispensable garment.

The next morning, Stockbridge – and, for that matter, the whole of Berkshire County – had something to talk about, and they have been talking about it ever since.

(To be continued.)


[i] I have been writing about the Berkshire cottages for 35 years and never knew the name of Charles Southmayd’s cottage. I and other writers were content to call it Southmayd’s. I stumbled over the name “Eastview” quite by accident in the Town of Stockbridge Annual Report 1909.

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