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Sagas of the Shire: The Mystery of the Gentleman Burglar
By Joe Durwin, iBerkshires Columnist
07:43PM / Sunday, October 25, 2015
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STOCKBRIDGE, Mass. — It began as an isolated incident — a widow on the outskirts of town, robbed at gunpoint by a masked intruder who slipped in quietly, in broad daylight one warm afternoon that October.

She had just recently withdrawn $100 from the bank, which the masked man demanded. The witness said she was terrified until the robber spoke, which he did in such "soothing tones" that it calmed her considerably for the duration of the heist.

So began what The New York Times would refer to as "a reign of terror" for the town of Stockbridge, lasting from late 1892 through 1893, and give birth to the "Gentleman Burglar," a criminal of folkloric dimensions whose identity remains still debatable over a century later.

Similar larcenies followed only a few days later. Another widow, Mrs. Moore, awoke to  find the prowler in her bedroom.  She too had just received a sizable sum of cash that day, which the burglar demanded, "in a suave and gentle tone."

Mrs. Moore would describe the man as tall, about 6 feet, and well dressed. A fine handkerchief covered all but his eyes, and his hands appeared small and soft, she said.

The following night, the burglar tussled with Charles Southmayd, a 70-year-old attorney, escaping with $200 in cash Southmayd had just withdrawn that day.

Stockbridge reacted with growing alarm, as houses around the village reported attempts at break-ins over the next few nights. Men were organized into watches to guard against the culprit, and remaining cottagers fled back to New York.

With them left the burglar, it seemed, as by the first snow in November incidents had ceased, and as months wore on no more sign was seen of the masked man.  

Not long after the summer crowd returned, though, the robberies resumed.  

At the Parke cottage on Main Street, the burglar entered through the kitchen and robbed the two women present, Mrs. John Swan and her friend Miss Stetson, who was staying as a guest.  

It is due in part to Miss Stetson that this Stockbridge thief's reputation took on something of mythic proportions.

"Every inch the gentleman," Stetson recalled of him, with a voice "low, soothing, musical and even mesmeric in its effect."

His other victim that night was less charmed by his demeanor. Laura Field, daughter-in-law of famed law reformer David Dudley Field, lashed out at him as he attempted to remove a valuable watch from her bedroom. Field threw herself on the masked miscreant and would not let go, shouting for help even as he dragged her across the room and warned pleadingly that he would have to shoot her if she wouldn't let him go.

Hearing her cries, a valet appeared, then in a classic bit of Victorian crisis management excused himself from the room, finding himself ill dressed for the hour and the company.  After tossing on a pair of trousers and a bathrobe, the valet reappeared, brandishing a relic pistol of Civil War vintage. He managed to get off one frantic shot through the front door from which the burglar had just departed.  

Based on accounts of his demeanor and the apparent knowledge the thief seemed to have of his jet set targets, police at first surmised that he might be one of their butlers.  This theory was quickly discarded after a subsequent break-in when the emboldened burglar woke the household with the loud popping of a bottle of champagne he'd helped himself to, an offense for which no competent resort butler could be suspected.

Stockbridge society seemed simultaneously terrorized and titillated by his prowlings, and all that season could talk of little else. Locks were installed all around town, New York City detectives called in, and rewards raised up to $1,350 for information leading to his capture.  

For months, though, nothing could bring to heel the mysterious interloper, who by now metropolitan papers were beginning to call the "Gentleman Burglar," as they further romanticized his genteel demeanor with his mostly female victims.

"No one, unless he has visited the town, can understand or realize how deep-seated and widespread has been the terror diffused through Stockbridge," wrote the New York Times in September.  "That this historic village, redolent with its reminisces and intellectual vigor, should be cowed by one man, is incredible to the average native Massachusetts citizen."

On Oct. 27, the Gentleman Burglar reached the height of his pilfering, entering the Sedgwick home during a party. Going directly to the wine cellar, he liberated a 3 1/2-gallon demi-john of wine. From there, he proceeded to burglarize two homes, four downtown stores, and a passerby from whom he extracted 50 cents at gunpoint.

Alarm spread from Stockbridge to Lenox two weeks later, when a fearsome burglary was carried out against the Rev. William Grosvenor and his family at the rectory of Trinity Church.

This time, four masked burglars appeared, waking the clergyman and his large family from bed and herding them into the hall while they ransacked the house for valuables. The gang worked quickly, then escaped with a carriage and horses stolen from a nearby barn.

Despite the differences, the burglary at the rectory was believed to be connected to those ongoing in Stockbridge, and overall rewards were raised as Lenox, too, now armed itself and began installing locks.

The imperiled peace of mind of so many affluent members of New York society put significant pressure on city police detectives to put a stop to the break ins, and it was one of these who first noticed similarities of these crimes to some that had been plaguing much the same social set at properties in Long Island and Connecticut.  

Detective Sgt. Stephen O'Brien, a talented investigator renowned for the capture of many prominent felons, was ultimately responsible for the collar of several men believed to be connected with the burglaries in Berkshire and elsewhere.  

The three suspects, Michael Sherlock, William Mahoney, and Edward Fitzpatrick were arrested on New Year's Eve at the entrance to the 34th Street ferry, so surprised by the descent of officers with guns drawn that Sherlock is said to "have nearly fainted."

It was Michael Sherlock who authorities proclaimed to be the "Gentleman Burglar" of Stockbridge notoriety, though police recovered property linking all three suspects to robberies in both Stockbridge and Long Island.

Sherlock was identified as the marauding "Gentleman" of Stockbridge principally by his height, his small hands, and his voice, the soft sound of which had so impressed many of his female victims. From New York, he was extradited to Massachusetts to stand trial in Pittsfield.

In the meantime, another suspect for the sensational burglaries had been apprehended for a heist in Connecticut, and was convicted in Bridgeport in March. Described as soft spoken and exceedingly well mannered, Thomas Kinsella Jr. also happened to be a native of Stockbridge, where he had until recently spent most of his life.

Kinsella appears, under historical reconstruction, a complex and in some ways tragic figure.  

Born in Stockbridge in 1857, Kinsella had emerged from a troubled orphan youth in which he spent at least some time in reform school to become a skilled stonemason whose work could be seen in a number of the local cottages, most notably Naumkeag. Things took a turn for Kinsella in the mid 1880s, though, beginning with the deaths of four of his seven children from diptheria within a 13 month period. Two years later, Kinsella accidentally shot and killed his mother in law, Elizabeth Bannon, serving two and a half years for manslaughter from 1887 to 1890.

By the spring of 1894, both Kinsella and Sherlock had been variously dubbed the "Gentleman Burglar" by various sources, while some speculated that there may be some connection between the two.

This was borne out by one of the principal witnesses for Sherlock's prosecution, Kinsella's second wife, who elaborated on the organized gang of burglars that had been run by her husband, in which Edward Fitzpatrick was second in command and Sherlock occupied the No. 3 position.  

Jennie Kinsella told investigators that from the Brooklyn home, Kinsella had orchestrated the gang's burglaries in Stockbridge, Long Island and Bridgeport and gave up names of numerous associates serving under him.

While awaiting Sherlock's trial, Jennie Kinsella was put under police protection, though her security detail gradually dwindled to one officer, and overlooked her extensive drinking and stream of booze-filled parties at her apartment. On July 19, the day before she was to travel to Pittsfield to testify, she was found dead.

Suspicious were aroused, though the examining physician declared her death a result of illness exacerbated by drinking.  

The absence of Kinsella's testimony did nothing to change the outcome of the trial for Michael Sherlock, who was sentenced to 15 years time at the Charlestown State Prison, after which no further records of him can be found.

Kinsella served a similar sentence in Connecticut for the Bridgeport heists, and upon his release in 1909 returned to work as a stone mason. He moved to Pittsfield and, at the time of the 1930 Census, was living on Bradford Street with his son and daughter in law.  In 1931, his son had him involuntarily committed to the state mental hospital in Northampton, where he died in 1932 at age 76.

In the intervening century, sources have varied on the identity of the so-called "Gentleman Burglar," some say Kinsella, some say Sherlock. Neither explicitly confessed to the crimes in question, and both had attributes fitting the description of the character that so befuddled the village of Stockbridge for more than a year.

It is known, however, that the two were working as associates on a string of robberies enacted upon high society across three states. Given the slight discrepancies of witness accounts, and the nature of the robberies, typically at multiple locations in a single night, suggest that the "Gentleman" in question may have been a combination of both men, and possibly others in the gang as well.  

The story of the Gentleman Burglar that became so broadly told in news across the country and internationally inspired a sizable body of melodramatic fiction over the decades that followed, and is still remembered in most accounts of that cottage building period, as well as a major historical highlight for the Stockbridge Police Department.

We may never know for sure whether the legendary character that loomed so large in Berkshire gossip those two seasons was a single individual or an amalgam of more than one perpetrator, but the somehow charming sweep of criminal exploits would forever leave its mark on the story of New England's Gilded Age.

This column is born out of an attempt to break new ground, or at least break out of a certain habitual mold of local history storytelling. While the Berkshires have enjoyed many great historians and much outstanding historical writing, it is my belief that there is a great deal that may have fallen by the wayside in its attempt to hammer out a unified narrative in its vision (and marketing) of itself. 

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