During 1874-5, a new jail was built on the corner of Main and Pine streets in Edgartown. Pressure to move the jail had begun about five years earlier, when the state instructed the county to expand its courthouse to accommodate a fireproof vault. The old jail, located about where the Registry of Deeds is today, had to go.
The old, four-room jail was not heavily used. In 1871, the Massachusetts Commissioners of Prisons criticized it as an “extreme” example of “extravagance”; that year a single prisoner occupied the jail for nearly five months, at a cost to taxpayers of $329. In 1872 they noted, “The rooms are seldom occupied, and ought never to be except as a place of detention for a short period.”
But when the new jail opened in 1875 under the watchful eye of Sheriff Francis Smith, it boasted 12 cells (still in use today), even though in its early years, the sheriff and his deputies “promptly send back to the main those who show a disposition to break the peace,” according to the commissioners’ reports. The jail averaged about two prisoners at any one time during its first few decades. In 1885, for instance, a total of eight prisoners spent time behind bars during the year — seven for drunkenness and one for larceny. “This jail, though small and little used, is a pattern for neatness and good order. The building is empty for the larger part of the time.”
By 1919, little had changed. The Boston Globe reported, “The prisoners are so few in number that sometimes the number of attendants required to man the institution properly is greater than the total number of inmates.” Comparing the Edgartown jail to those elsewhere on the Cape and Islands, the New Bedford Standard remarked, “Either because the bad folks on the Island who get into the Edgartown jail are less interesting or always well cared for, the Island jail has been less in the public eye.”
But things got interesting later that summer, when Joe “Lefthander” Swartz of Oak Bluffs was arrested for a nighttime burglary. While he was detained in a holding cell at the Oak Bluffs police station, an accomplice managed to pass him a crowbar, and Swartz made his escape. He was soon recaptured and delivered to the jail in Edgartown, under the supervision of jailkeeper Eben Earl. He didn’t stay long.
“Last Monday,” reported the Boston Globe, “[Swartz] was given the privilege of walking in the jail corridor while the keeper is said to have gone to the movies. The keeper is said to have hidden the key of the jail, but someone from the outside located the key, and Swartz continued his promenade from the lockup corridor to the great outdoors.” When Earl returned that night and checked on his prisoner, he was fooled by a roll of clothing fixed to look like a human figure. Swartz’ escape was not discovered until breakfast was delivered the next morning.
A home break-in was soon reported. Investigators spotted a nearby figure, and although the man’s clothing and complexion didn’t match Swartz’, his distinctive walk gave him away. “Escaped Edgartown Prisoner Makes Up as a Movie Star, but His Walk Betrays Him” read the headline in the Boston Globe after Swartz was discovered to have disguised himself with white paste and powder. He was promptly returned to the Edgartown jail.
A week later, he escaped for the third time. Earl had locked the cell door for the night, put the key in his pants pocket, and went to bed, with his trousers deposited nearby. As the keeper slept, an accomplice of Swartz’ was believed to have crept into his bedroom, stolen the key, and delivered it to Swartz, together with a saw. Swartz unlocked his cell door, allowing him access to a locked corridor. He then sawed through the bars in the corridor window, and escaped for his third and final time. He broke into a store, stole some cash, stowed away on the Uncatena, and was well on his way to Providence or Boston before his disappearance was discovered. Earl quit.
But while our local authorities may have lost a few, they sometimes managed to catch a few as well. In 1922, John William Silva of New Bedford and Fall River, known to Massachusetts police as “the Human Fly” (named, according to the Boston Globe, for his “daredevil stunts”), escaped from Rutland Hospital, where he was being treated during a two-year sentence for burglary at Charlestown State Prison. Silva took refuge in Edgartown, but raised suspicions among the locals. He was identified, arrested, and taken into custody by Sheriff Walter Renear, and promptly returned to the mainland by a state detective.