The state's first prison, Old New-Gate, built in 1773, was a former copper mine where the worst criminal offenders were sent to do hard labor. Convicts were kept in the mine's two shafts, one at 25 feet and the other more than 60 feet below ground. Escape seemed highly unlikely.
But the depth of the mine shafts didn't prevent breakouts. The first prisoner escaped just 18 days after the prison opened.
Over the half-century Old New-Gate served as a prison, about 10 percent of its 950 prisoners freed themselves. Some were caught and returned, rewards paid. Others got away.
Prisoners' yearning to be free hasn't abated in modern times. Since 1968, more than 950 escapes have been recorded from the state's 19 prisons.
'Cunning As A Viper'
In 1773 Capt. John Viets, who had worked in the New-Gate copper mine, was appointed the first master of the prison in what was then part of Simsbury — now East Granby. The same year he also was granted a tavern license. Viets sometimes allowed certain prisoners to leave their cells and have a drink at his tavern, just across the road.
John Hinson was unlikely to get such special treatment. On Dec. 22, 1773, the 20-year-old burglar and con man was the first criminal confined to New-Gate prison. According to the Colebrook Historical Society, when Hinson was turned over to Viets, the judge warned that "he is sly, ornery and cunning as a viper. If there is any way of breaking out of Simsbury jail, Hinson will find it."
Eighteen days later, Hinson did just that.
On a snowy January evening, Viets checked on his prisoner and found only an empty bed. Hinson's personal belongings were gone, and so was he.
A letter to the General Assembly dated Jan. 17, 1774, from the prison's three overseers described the escape: "We the subscribers, overseers of New-Gate Prison, would inform your Honors that New-Gate prison is so strong and secure that we believe it is not [possible] for any prisoner out there to escape, unless by assistance from abroad: yet it so happens that one John Hinson … has escaped by the help of some evil minded person at present unknown, who in the night … drew the prisoner out of the shaft."
Hinson's departure led to another Connecticut first: a classified ad offering a reward for an inmate's escape from a state prison. The week after Hinson's escape, The Courant published an advertisement placed by Viets, offering $10 to anyone who "will take up said fellow and return him to the subscriber … of said prison, or shall discover those that aided him in his said escape, so that they may be brought to conviction."
No record of Hinson's return to New-Gate was found. Hinson's escape, and the ad that followed, wouldn't be the last.
Record-Setting Escape Artist
Richard Steel once appealed to the state legislature to be put to death rather than sentenced to hard labor at New-Gate. He had chosen a life of crime, he said, to avoid hard labor and would rather die than live against his principles.
Steel believed in those principles enough to set a state record, escaping from prisons all over Connecticut, including three times from New-Gate.
Steel was a repeat offender. He was already known as a "notorious burglar" in the earliest Courant reports of his criminal exploits in April 1771. An ad placed by Hartford County Sheriff Ezekiel Williams offered a 40 shilling reward for the return of Steel, who had again escaped from irons, having "been twice crop'd and branded" previously.
Steel was recaptured later that month in Fairfield, having put up a "vigorous resistance and wounded the person in the head … who took him in," The Courant reported.
He evidently escaped again, as he was returned to Hartford from a jail in Boston in September 1774. The Courant published the sheriff's list of valuable items found with Steel, so that they might be returned to their rightful owners. Among them: "a black horse colt 2 years old… a good saddle; with a saddle cloth almost new… a neat pair of pocket pistols… a fine ruffled shirt…a single cased silver watch."
Steel was confined to New-Gate, but not for long. On Nov. 21, 1774, he escaped with five other men. Rewards were offered and four of the men were quickly returned. Advertisements ran in the Courant on Nov. 28 and Dec. 5, 1774, for the fifth prisoner. It was Steel.
A typical advertisement for an escaped prisoner in the 1770s included a physical description of the missing inmate. The ads for Steel's return that ran in The Courant said he was "so well known as to need no description."
Steel was returned to New-Gate, but it took less than two months for Viets to again place an ad, as Steel escaped with three other inmates in June 1775. By July 1775, Steel was again back at New-Gate, according to an ad published about the search for two of the men.
Steel would make one more escape from New-Gate on Aug. 24, 1775, but did not return. According to an account in The Courant, he joined the British army, deserted, was captured and executed.
Two British loyalists, Captain Ebenezer Hathaway and Thomas Smith, were captured from the privateer boat Adventure while it was anchored off Long Island in Huntington Bay on April 7, 1781. The men were brought ashore in Stamford, transferred to Hartford and sentenced to New-Gate.
Less than two months later, the Connecticut Courant reported a prison breakout that remains the largest in the state's history. A crowd of prisoners, including the Tories Hathaway and Smith, rushed the New-Gate guards on the night of May 18, killing one and wounding others, and took off with the guards' weapons and ammunition. Twenty prisoners escaped.
On May 29, 1781, The Courant reported that "Sixteen of the prisoners who made their escape from New-Gate last week are since taken and returned to their former lodgings."
Hathaway and Smith were among the four who were still on the loose. They reached British-held New York and published their escape story in the New York Royal Gazette.
When Old New-Gate closed in 1827, 81 prisoners were transferred to a new penitentiary in Wethersfield. The Connecticut State Prison was a maximum-security facility, but the escapes continued.
The Derby Poisoner
The new prison added a women's wing in 1831, and Lydia Sherman was one of its most famous occupants, until she walked away from the prison in 1877.
Sherman was known in Courant headlines as the "Derby Poisoner," the "Wickedest Woman" and the "Woman Monster." The confessed killer of three husbands and at least four children, whom she poisoned with arsenic, Sherman was sentenced to life in Wethersfield for those crimes in 1872.
On the evening of May 29, 1877, The Courant reported, Sherman slipped out of her cell, which had been kept unlocked due to her "precarious health," while the prison matron was inspecting the upper tier of the cell block.
Sherman hopped a train to Springfield, carrying $30 from odd jobs she'd done for former convicts and the sale of "fancy work." Before leaving on a train to Worcester, she bought a few necessities — "a traveling dress, a morning dress, toilet articles, towels, a fan, perfumery, etc.," according to her own account, published in the Courant.
With no set plan, she continued on to Providence and checked into the Central Hotel, registered as Mrs. Brown from Philadelphia.
"I didn't really lie," she explained in The Courant's story, "when I said I came from Philadelphia, for I really lived there once. But I wasn't going to say I came from Wethersfield."
Hoping to get work, Sherman befriended the hotel's landlady, Mrs. Sears. Forgetting the name she'd registered with, Sherman used the name Mrs. Moore in conversation.
"That was my great mistake," Sherman told The Courant.
Sears contacted the police, who questioned Sherman. The police presented her with a napkin ring bearing the name "Lydia" that had been among her possessions, and she responded that it didn't say "Lydia Sherman" on it. However, the detective had not yet mentioned Sherman's last name. The jig was up and this confirmed her identity for police.
"Mrs. Sherman expressed herself as glad to get home," The Courant report said when she returned to her quarters in Wethersfield.
Sears received a $500 reward.
Ice Box Bandit's Wild Ride
Albert J. Raymond, along with Roland Lalone, terrorized Massachusetts and Connecticut meat markets, emptying cash registers and leaving shopkeepers locked in their ice boxes. The two criminals were both sentenced to life in Wethersfield State Prison in September 1928 for killing Pomfret policeman Irving H. Nelson in a shootout after one of their heists.
Raymond was a model prisoner, earning the "trusty" title. After 11 years at Wethersfield, he'd held jobs as clerk to the deputy warden and waiter in the officers' dining room. He played clarinet in the prison band and won a prize for prison periodicals when he served as editor of the Wethersfield's "Monthly Record."
In April 1939, Raymond was given a position working as a butler and houseman in the home of Warden Ralph H. Walker and his wife. The position was sought after by prisoners, according to The Courant's June 12, 1939, report of Raymond's escape.
Walker and his wife were away from their home on the morning of June 11, and Raymond was alone in the house with their son, Albert Walker. Raymond walked out the front door of the house, which faced away from the prison, got in Albert Walker's 1937 convertible Ford coupe and drove off.
Albert Walker didn't notice the missing car, or the missing convict, until around noon. He notified authorities but Raymond had a three-hour head start.
"Connecticut was encircled by police in little more than a half hour after the break was discovered," The Courant reported. "About 20 cruisers were sent out on all main highways, each car carrying a State Policeman and a prison official who knew Raymond by sight."
The Ford had three-quarters of a tank of gas, with the potential to travel about two hours, and Raymond wasn't carrying any money. Police in 11 states were notified of the escape.
A break came when a gas station operator in Putney, Vt., reported selling five gallons of gas to Raymond around 3 p.m.
The convertible was spotted by Vermont police just before 6 p.m. and, according to The Courant, a "wild 85-mile an hour chase from Bellows Falls, Vt., to North Clarendon," ensued, ending when Raymond was forced to swerve the car to avoid a head-on collision. He crashed into a culvert and was taken to Rutland Hospital with a broken arm, broken rib and multiple abrasions.
Police discovered that a former liquor smuggler known as "Little Joe" who was serving time at Wethersfield had given Raymond the route from Connecticut to Canada. They never discovered where Raymond got the $10 he used to pay for the gas in Vermont.
A Handcuff Key In Peanut Butter
In the last half-century, the state's prison system expanded to more than 20 facilities. Wethersfield closed in 1963 and 788 prisoners were transferred to a new maximum-security state prison in Somers. Since Jan. 1, 1968, when the state Department of Correction was established, there have been 964 escapes by 880 inmates – some escaped more than once. All of those escapees were returned to confinement, according to the Department of Correction.
Among those modern-era escapes was Frederick Rodney Merrill, dubbed the "Peanut Butter Bandit" after his mother hid a gun, money and a handcuff key in a Christmas gift of peanut butter. Merrill used the gun to escape from guards during a transfer from court back to Somers prison in 1968. He was caught at a police roadblock, fleeing with his mother.
Merrill was not the lighthearted guy his nickname implied. He went on to serve sentences in Connecticut and Canada for violent sex assaults and multiple prison breaks.
Escaping Two Prisons In One Day
Anthony Germani was a Rhode Island mobster already convicted of two murders when he managed to escape from two Connecticut prisons in one day.
Germani, 37, was being held at Osborn Correctional Institution in Somers on July 9, 1992, when he switched clothes and ID cards with his cellmate. The cellmate was scheduled for transfer to minimum-security Camp Hartell for drunk drivers in Windsor Locks.
Germani escaped the Windsor Locks facility over an 8-foot fence. It took about three hours for authorities to realize what Germani had done.
Authorities were bracing for a violent capture, given Germani's record. He had served 15 years in prison starting at age 20, convicted first for shooting a man during a drug robbery, and once in prison, for helping to kill a former police officer who was serving a sentence for selling heroin.
East Granby Constable Andrew Rossetti, 32, recognized Germani on Route 20 two days after the escape, thanks to the convict's red sneakers and a tattoo of a bird with the name "Debbie" on his arm. After two nights in the woods, tired and covered with mosquito bites, Germani gave up without a fight.
There have been 19 prisoner escapes from Osborn, the state's only maximum-security prison, since the state started keeping records in 1968. And state correction officials emphasized that Germani "didn't physically breach the fence or the alarm system."
As a department spokesman explained in The Courant on July 10, 1992, "To me, the way we're looking at it is that it was an erroneous transfer from Somers to Hartell and then an escape from Hartell."