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bootlegging

Prohibition in Vermont and the Legend of Catherine Dillon

Prohibition in Vermont started early. Liquor officially became illegal in parts of Vermont in the early 1800s, with towns demanding the right to outlaw sales of alcohol within their borders. In 1850 the state officially banned licensing alcohol-selling establishments and two years later banned all manufacturing of alcohol. With that, the state went dry – sort of.

New York City Deputy Police Commissioner John A. Leach, right, watching agents pour liquor into sewer following a raid during the height of prohibition (Library of Congress)

Enforcement of prohibition was always a spotty affair, with each town and county taking its own approach to policing liquor sales. In some places, alcohol virtually went underground. But others openly tolerated saloons, though the growing temperance movement in the country began pressuring Vermont cities and towns to crack down on the “rum holes” in their midst.

Vermont’s remote northern border was always popular with bootleggers. Bringing liquor surreptitiously from Canada to avoid taxes was a common enough activity. But with the change in the laws in 1850, it became far more attractive. The crackdown on domestically produced liquor pushed the demand for bootleg hooch through the roof. The border region became a hotbed for bootlegging right through the era of nationwide prohibition in the 1920s.

Catherine Dillon Comes to America

Into this turbulent environment came Catherine Dillon. If you were given just two words to describe Catherine, you wouldn’t go far wrong with “beautiful” and “feisty.” She came to America in 1851 to Oswego, N.Y. at roughly the age of 25. Catherine (maiden name Driscoll) was part of the wave of Irish immigrants who poured into America. Famine, political persecution and economic recession in Ireland made America look like a paradise of jobs and opportunity.

In northern Vermont and New York, the railroads provided jobs for the Irish. Catherine Dillon, meanwhile, decided to provide them with everything else — food, shelter and drink.

Following the workers as they migrated from railroad to industrial jobs, Catherine moved from Oswego to Rouses Point and finally across into Vermont, spending time in Swanton and finally settling in St. Albans. There she and her husband, Patrick, began assembling a small village of tenements populated with her fellow Irish immigrants. In addition, she offered alcohol at two saloons, and it didn’t take long for the law to notice.

In December of 1854, in Franklin County Courts, Catherine and Patrick were fined $40 for illegally selling liquor. Patrick went to jail for failing to pay the fine. And in December of 1855, Catherine was back in court, this time sentenced to three months in prison.

Courts and Jails

Catherine fought the charges with a vengeance all the way, at one point losing her case only because her lawyer didn’t get an appeal filed fast enough.

In March of 1856, the police found six barrels of liquor on her property during a raid. No one was willing to step forward and admit they owned the booze, and so it was ordered dumped.

Around 1857 she sought a divorce from Peter. She claimed he was abusive. Peter argued that anyone who knew Catherine knew he was no match for her. The story of how she finally rid herself of Patrick goes like this: One day they arrived back in Vermont on a train and Patrick went to collect their luggage. Catherine pointed out a suitcase and told him to take it. It didn’t belong to her, however, and she reported her husband to the police and had him jailed. The incident was enough to send Patrick packing, off to the Army as a bugler. How much of the story is true and how much is legend remains a mystery, but it was reported in her obituary.

Meanwhile, Catherine’s legend grew. In one instance, a man died after getting drunk in her saloon. She initially faced manslaughter charges, but they were dropped. In other cases, she would be arrested, only to escape and be back in business within days. The ease with which she navigated the legal system left many wondering if she wasn’t managing to corrupt the police.

Prohibition in Vermont Gathers Steam

By 1865 the calls for putting a stop to liquor sales were growing louder. In 1868 Catherine was convicted of smuggling liquor from Canada and fined $1,500. She disappeared, leaving the sheriff to seize her animals and property to settle the fine. In another case, two men claimed she waved a pistol at them when they approached her about paying a bill.

While prohibition in Vermont still had a long run ahead, Catherine Dillon did not. Finally the persistent fines and costs of fighting in court got to Catherine, and she gave up the liquor trade around 1870. Whether she would have stayed out of the business is a moot point. In September of 1871 Catherine suffered $5,000 in losses when a fire swept through St. Albans and destroyed a large section of the city.

By this point Catherine was nearing the end of her life. At just 45 years of age, she died alone in her house. She left a considerable estate, including 125 acres of land, a farm, tenement houses and commercial buildings. Estimates put its value at somewhere between $50,000 and $75,000.

Catherine’s two brothers were the beneficiaries of her estate, though her death would eventually provoke a protracted lawsuit. A long-lost sister argued she was owed a portion of the estate. She charged that her brothers, though they knew how to find her, neglected to tell her that Catherine had died a very wealthy woman.

This story was updated in 2023.

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Vermont’s Disappearing/Reappearing Catherine Packard

In August of 1929, police in Chester, Vt., discovered the body of a young woman buried in a grove of spruce trees. They could not identify her by her remains. But police thought they might know her identity – Catherine Packard.

George Packard of Rutland, a candy store clerk, had reported his wife Catherine missing just months earlier. Catherine Packard, a troubled young woman, had two children. She had grown up as a ward of the Vermont Children’s Aid Society.

Charlotte Packard

Police presented George with a description of the dead woman they had found. Then they showed him a note found with the body. The suicide note said, “I am sick of life and I am going where I will be happy.”

An autopsy showed the girl in the field had poison in her system. George Packard identified the handwriting as belonging to Catherine. Clothing, dental records and the note convinced police that the body was, in fact, Catherine Packard. And then she was buried.

George, meanwhile, remarried in the summer of 1930 to Margaret MacFarland. But not everyone thought Catherine had died. The Vermont Children’s Aid Society refused to accept the proof that Catherine was dead. George’s mother had an insurance policy on Catherine’s life, but the insurance company refused to pay the death benefit of $459. The company said the proof of Catherine’s death was not certain.

Merchants’ Row in Rutland, Vt.

Then, in August of 1930, Vermont was shocked. Catherine Packard reappeared in Manchester, N.H. She was returned to Vermont and questioned. Packard had run off with Robert “Romeo” King, and the couple had been living together in Erie, Pa. Catherine said she was astounded to discover people thought she was dead.

Charlotte Moore Buswell

George, stunned by the reappearance of his wife, sued for a divorce, which was granted. He remarried Margaret MacFarland. King was prosecuted on civil charges for taking up with a married woman and sentenced to a short stay in jail.

But what of the girl in the field now buried under a headstone that read, “Catherine Packard?” Sheriff E.H. Schoenfeld stayed with the case, and in April of 1932 he announced he had discovered the identity of the dead girl. His discovery, however, did little to tamp down the sinister overtones of the case.

Charlotte Moore Buswell had been the prettiest girl in Chester. She had a short, unhappy marriage that ended in divorce. She began running a tearoom in nearby Bartonsville, Vt. In 1925 she disappeared. A friend, Ida Sweet, said she dropped Charlotte off at the train station in Bellows Falls. No one in her hometown, not even her family, ever heard from her again.

Bellows Falls Railroad Tunnel

But Sheriff Schoenfeld discovered that Charlotte had gone on to join in a rum-running and narcotics ring near Lake Bomoseen. Vermont was a prime location for bootlegging during Prohibition. The border with Canada was loosely patrolled and remote. Illegal liquor flowed steadily. The state’s resorts, lake houses and line houses were convenient for visitors from New York and New England looking to quench their thirst for alcohol away from home.

Lake Bomoseen

The resorts at Lake Bomoseen roared in the 1920s. More than 500 hotel rooms crowded the shore. Searchlights crisscrossed the night sky drawing thousands of visitors to its dance pavilions. And despite Prohibition, the booze and drugs were available for the right price in secluded spots.

Lake Bomoseen

Charlotte Moore Buswell had gotten caught up in the rum-running life around Lake Bomoseen, the sheriff said. She had been fined $300 for bootlegging in Rutland, after she “disappeared” from Chester. And then she turned up dead. Given the company she kept, her death didn’t shock anyone. But what about that suicide note? George Packard had not been wrong. His wife had written the note.

Catherine Packard said she had, in fact, written the note. But she could not explain how or why it wound up on Charlotte Moore Buswell’s body. Catherine said she wrote the note while training at a hospital in Troy, N.Y., in 1926 at a time when she felt despondent. It had nothing to do with her disappearance, she said. She theorized that someone had perhaps stolen it from her belongings at the hospital. And with no further proof, that’s as far as the mystery ever went.

Thanks to the Ticonderoga Sentinel and the Plattsburgh Daily Republican. This story was updated in 2021. Images: Images: Lake Bomoseen, By Jc3s5h – Own work, CC BY-SA 4.0, https://commons.wikimedia.org/w/index.php?curid=44282020. Bellows Falls Railroad Tunnel By Beyond My Ken – Own work, CC BY-SA 4.0, https://commons.wikimedia.org/w/index.php?curid=60091060.

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Carl Rettich, The RI Mobster Who Invented Cement Shoes

When Carl Rettich moved to a seaside mansion on Warwick Neck in Warwick, R.I., people thought he was a genteel lawyer named Charles Ryerson who moved to the neighborhood to take care of his elderly father.

The crime castle of Carl Rettich. Photo courtesy Boston Public Library, Leslie Jones Collection.

He actually belonged to the mob and had links to Al Capone.

Carl Rettich

The New Jersey-born Rettich got involved with New York’s criminal underworld at 17. He overheard a plot to kill a wholesale poultry dealer, but kept his lips sealed about the murder. That got him started in the mob-controlled live poultry business. He soon moved on to bootlegging.

Suspected of a 1924 murder in New York, Carl Rettich moved to Rhode Island to run New England’s biggest crime ring during Prohibition.

When the truth about ‘Charles Ryerson’ emerged, so many people flocked to ogle his crime castle that an ice cream vendor showed up to sell his wares.

Prohibition

When Prohibition took effect, speakeasies sprang up all over Rhode Island (and elsewhere). Illegal hooch flowed freely in Kent County: in West Warwick, Old Warwick, Warwick Neck, Arctic, Apponaug and East Greenwich.

Smugglers operated with impunity along Rhode Island’s rugged shoreline, where quiet inlets and coves disguised their activities.

Danny Walsh, a prominent Rhode Island horse breeder, controlled the liquor smuggled into Rhode Island. Carl Rettich joined Walsh and began expanding operations. He bought the 20-room mansion overlooking a cove. The press later nicknamed it the ‘crime castle’ and ‘murder mansion.’

Carl Rettich

He lived large on Warwick Point. People said Rettich threw parties for politicians and ‘high-hat’ friends, during which he showed off his machine gun by firing it on the front lawn. The estate was so isolated the neighbors didn’t complain.

Carl Rettich also had a fleet of speedboats tricked out for smugglers’ every need. They each had three Liberty airplane engines and were plated with armor and layers of New York telephone directories. They would speed out to the 12-mile limit, where they unloaded bootleg liquor from seagoing vessels. Then the rumrunners brought their contraband to a stone dock leading to Rettich’s crime castle. They stored the booze in a secret underground vault before distributing it.

Then Danny Walsh and Carl Rettich had a falling out. Walsh disappeared in February 1933 a day after they argued in public. Rettich was suspected of accepting a ransom of $40,000 for Walsh and then doublecrossing Walsh’s family.

Grisly Tale

The Associated Press ran a story on June 3, 1935, speculating that Walsh ‘was stood in a tub of cement until it hardened about his feet, and then thrown alive into the sea.’ The AP reported it was just a ‘grisly underworld tale,’ and no witnesses had been found.

Police kept looking. An informant tipped them off to Rettich’s criminal activities. He told them Rettich’s crime castle contained a secret vault and an underground tunnel.

In April 1935, police acted on a tip. On the banks of Lake Pearl in Wrentham, Mass., they found the body of Andino Merola slumped over a Chevrolet with a .38 bullet in his head. Merola was a small-time associate of Carl Rettich, and police believed he was involved in the murder.

In July, police got a warrant to search the crime castle. They combed the property, but found no tunnel, no vault. The basement was spotless, with four whitewashed brick posts.

A Few Beer Cans

One detective thought the basement looked too clean. He looked carefully and found a large screw in one of the posts. When he turned it, the cement floor rose slowly to the ceiling, revealing steps that led to a concrete room. But they only found a few beer cans in the room.

Police discover the secret vault. Photo courtesy Boston Public Library, Leslie Jones Collection.

On the rest of the property, though, police found an arsenal of weapons, a car with bullet holes in it and stolen money.

Police eventually accumulated evidence implicating Rettich in the disappearance of Danny Walsh, a dozen Massachusetts bank robberies and four murders.

As details about the real Carl Rettich emerged, his crime castle took center stage. On May 5, 1935, a crowd of 15,000 people came to rubberneck the 20-room mansion.

Cement Shoes

Informants told police that Rettich’s gang took Walsh to a dungeon and clubbed him on the head. They put his body in a barrel filled with concrete and dumped it into the ocean.

His girlfriend talked too freely about what happened to Walsh, they said. Rettich’s men took her to the underground vault, killed her and put her feet in a tub of wet cement. Then they dumped her into the ocean. Putting a whole body in wet cement was just too heavy.

No one ever found their bodies. But Carl Rettich spent the rest of his life in prison anyway, convicted on multiple charges for a Fall River mail heist that netted $129,000.

Carl Rettich built his crime empire with help from corrupt public officials. Prosecutors later discovered that Rettich and his gang had paid off Warwick police for three years. An investigation uncovered the bribes, and 11 police officers left the force.

This story was updated in 2023.

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Gentleman Gerald Chapman, Connecticut’s Celebrity Gangster

Gerald Chapman, Prohibition’s celebrated “Gentleman Bandit,” might have escaped the gallows if he hadn’t gone on a crime spree in Connecticut.

Gerald Chapman. Photo courtesy Boston Public Library, Leslie Jones Collection.

While in prison, Gerald Chapman found a mentor who taught him that dapper dress and good manners diverted suspicion from criminal activity. Before he pulled off the biggest armed robbery in history, Chapman dressed well, lived in New York’s posh Gramercy Park neighborhood and frequented expensive nightclubs. He even affected a British accent.

Newspapers nicknamed him the “Count of Gramercy Park” and the “Gentleman Bandit.” He was the first celebrity gangster and the first criminal the press dubbed “Public Enemy No. 1.”

Gerald Chapman

Gerald Chapman came into this world as George Chartres in Brooklyn, N.Y. — or maybe it was Manhattan’s Lower East Side – sometime in August 1887. As a youth he drifted into petty crime.

Police arrested him for the first time at the age of 14, and he spent most of his young adulthood in Sing Sing. He met his mentor, George “Dutch’” Anderson, after his transfer to Auburn Prison.

Anderson’s real name was Ivan Dahl von Teler. Born into a wealthy Danish family, he attended Heidelberg and Uppsala universities. Then he dropped out of the University of Wisconsin to take up crime. Anderson saw in the younger Gerald Chapman someone who had enough smarts and daring to commit big-time heists.

Prohibition

Gerald Chapman in his Wethersfield prison cell. Photo courtesy Boston Public Library, Leslie Jones Collection.

When the two men were out on parole in 1919 they formed a gang with Charles Loerber, a getaway driver. He posed as their chauffeur while they plotted their crimes. Chapman pretended to be an oil baron, and Anderson his business partner. The gang quickly seized the opportunities presented by Prohibition and began bootlegging in the Midwest. They also arranged confidence scams on the side.

In 1921 they branched out into armed robbery. They plotted the route of a U.S. mail truck that ran regularly along a street in New York’s Tribeca neighborhood. On Oct. 24, they blocked the mail truck with two cars and assaulted the driver. Chapman and his gang made off with $2.4 million in cash, bonds and jewelry – the biggest heist in U.S. history.

They should have lain low, but instead they committed a string of robberies in upstate New York. But robbing the post office is a federal crime, and federal investigators soon hunted them down.

3rd Time the Charm

An undercover postal inspector nabbed them when he bought stolen Argentine gold notes from Gerald Chapman. He and Anderson were tried and sentenced to 25 years in the Atlanta Federal Prison.

Gerald Chapman then managed to escape after three tries. During his first attempt he tried to outrun a posse of 200 men. They shot him in the arm, kidney, hip and back. Six days later he escaped from Atlanta General Hospital, only to be captured again. After returning to the Atlanta penitentiary, he promptly broke out again and made a clean getaway in March 1923.

The press ate up the story of the Gentleman Bandit. Chapman paved the way for future celebrity gangsters like John Dillinger and Al Capone.

According to True Detective in 1929,

Newspaper feature writers used miles of typewriter ribbon on him, and ended by creating an idealized character which combined the daring of Jesse James, the ruthlessness of the apache, Clair Raoul, the suavity of Doctor Crippen and the ingenuity of the notorious Perugia, who committed the famous theft of the Mona Lisa.

Anderson escaped in December that year.

Death in New Britain

Gerald Chapman with his attorneys. Photo courtesy Boston Public Library, Leslie Jones Collection.sp

In the fall of 1924, Gerald Chapman and another man went on a crime spree in Connecticut. They were spotted trying to rob a New Britain department store, and five police officers rushed to arrest them. In the ensuing shoot out, Chapman killed Officer James Skelly and escaped. The police captured the other armed robber — Walter Shean, the ne’er-do-well son of a wealthy family from Springfield, Mass. Shean ratted out Chapman rather than hang for Skelly’s murder.

Gerald Chapman went into hiding at the farm of Ben Hance in Muncie, Ind. Three months later, Hance did his public duty and tipped off the police to Chapman’s whereabouts. Police arrested Chapman and sent him back to the federal prison in Atlanta.

Though the federal government had jurisdiction, the State of Connecticut wanted to try Chapman for murder. In March 1925 he was extradited to Connecticut State Prison in Wethersfield. His trial would turn into a media circus.

Awkward

Dutch Anderson ‘Wanted’ poster.

Ben Hance and Walter Shean testified against Chapman. The prosecution also showed that spent cartridges from Officer Skelly’s body matched Chapman’s gun. Chapman denied he’d ever been in New Britain. He also denied knowing Ben Hance or Walter Shean or that he was even Gerald Chapman.

The jury deliberated for 11 hours and on April 4, 1925 delivered a guilty verdict. He was sentenced to hang by the “upright jerker.”

“Death itself isn’t dreadful, but hanging seems an awkward way of ending the adventure,” Chapman then said to his attorney. The upright jerker, a flawed hanging mechanism, dropped counterweights to pull the victim upward. Theoretically death resulted instantly from a broken neck. But in practice victims sometimes strangled slowly.

Chapman’s lawyers argued the state couldn’t execute him because he had to first serve out his federal sentence. President Calvin Coolidge solved that problem by granting Chapman a pardon. Chapman appealed his sentence all the way to the U.S. Supreme Court, but the high court ruled against him.

Chapman was hanged until he was dead shortly after midnight on April 6, 1926.

Eight months later, Ben Hance and his wife were killed in revenge. They fell victim to a roadside ambush on the Anderson-Muncie Highway. Mrs. Hance died instantly. But Ben Hance lived long enough to finger Dutch Anderson and an accomplice. Police later killed Anderson in a shootout.

This story about Gerald Chapman was updated in 2022.

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Oliver Garrett, Boston’s Booze-Busting Million-Dollar Cop

When dashing Oliver Garrett was in charge of it during Prohibition, the Boston Police vice squad made 25,000 raids and 17,000 arrests in nine years.

It didn’t get any harder to find a drink.

Raid on the speakeasy at 153 Causeway St. 1932. Photo courtesy Boston Public Library, Leslie Jones Collection.

The mayor of Boston, England, visited the city in 1930 and proclaimed upon his return, “You can swim in liquor … you can drown in it.”

It didn’t take long for a crusading journalist to find out why: Oliver Garrett was on the take.

Oliver Garrett

Oliver Garrett. Photo courtesy Boston Public Library, Leslie Jones Collection.

Oliver Garrett was born Oct. 14, 1894 in Mechanic Falls, Maine. He served in World War I and joined the Boston Police Department in 1919, three months after Gov. Calvin Coolidge broke the police strike.

He rose through the ranks to head the vice squad in just a few years. He had plenty of work as Prohibition took effect in 1920. By 1928, Greater Boston had 4,000 speakeasies, including four on the same block as the central police station. Fifteen thousand people sold liquor, 5,000 of them full-time bootleggers.

Oliver Garrett quickly made a name for himself. He led raids personally, jumping from roof to roof and climbing through skylights. He seriously injured his hand in a raid in 1924 and broke his nose in 1927 when he dispersed a fight in the South End. Chinese gangs put a price on his life when he broke up an opium-smoking den in 1928.

The Boston Globe proclaimed, “No man was more feared by bootleggers than Garrett.”

Plain Talk

Suddenly in 1928 the Boston Police Department demoted Oliver Garrett to ordinary patrolman.

Journalist Walter Liggett offered an explanation in an article, “Bawdy Boston.” It appeared in the January 1930 issue of a highbrow magazine called Plain Talk. Liggett had spent a month in Boston investigating his favorite theme: The hypocrisy and crime spawned by Prohibition. He called bootlegging ‘the largest and best paying racket in Boston at the present time.’

To give some idea of the graft involved it merely need be mentioned that now, after ten years of so-called Prohibition, the people of Boston are spending at least $60,000,000 a year for illicit hooch…

Boston is literally honeycombed with speakeasies. There hardly is a building in town that does not contain at least one office where bottle liquor may be had. Most of these speakeasies are camouflaged as brokers’ offices, wool dealers or real-estate firms…Stylishly dressed women frequently purchased bottled booze over the counter while policemen lazily lounged in the front door.

Boat with sign “Fresh Fish and Fruit” delivers bottled drinks to men on pier (possibly Prohibition selling illegal alcohol). Photo courtesy Boston Public Library, Leslie Jones Collection.

Bawdy Boston

He attacked Mayor Malcolm Nichols and politicians who allowed crime to flourish. Liggett noted that many Cape Codders who helped the rum runners had Pilgrim fathers as ancestors. And he found ‘a certain grim humor’ in tracing the law that made those people into lawbreakers.

$175,000 in liquor seized in Dorchester Bay from rum runners. Photo courtesy Boston Public Library, Leslie Jones Collection.

The magazine sold out in Boston in one day despite efforts to ban it.

In “Bawdy Boston,” Liggett tagged Oliver Garrett ‘The Million-Dollar Cop.’ Though Garrett earned only $40 a week he owned a farm, a racing stable, a closet full of $150 suits, a Cadillac, a Marmon and a Chrysler. Liggett called him a bagman for higher-ups who dumped him because they didn’t get a big enough share of the spoils.

Garrett, insulted, resigned, claiming an injury in a car accident. Police Commissioner Herbert Wilson granted him his pension, setting off a firestorm of controversy. During the hearing that followed, the manager of the Ritz-Carlton testified that Garrett had forced him to hire a hat-check girl to accept payoffs to Garrett.

Indictment

In May 1930 he was indicted on charges of extortion. After several trials he pleaded guilty and was sentenced to two years in the Deer Island prison. Rumors flew that he had a motorboat to come and go as he pleased. He also supposedly had season tickets to the Red Sox.

Garrett got out of prison in 1933 and tried a career as a nightclub master of ceremonies. It didn’t go well. He sued the city for his pension and eceived $4,567 in 1952 – in exchange for a promise that he’d never sue the city again.

Oliver Garrett died Nov. 14, 1979 in Yacolt, Wash. He is buried in Vancouver, Wash., with his wife Althea.

With thanks to Drinking Boston by Stephanie Schorow and The Rascal King: The Life and Times of James Michael Curley by Jack Beatty. This story was updated in 2022.

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