Crime and Scandal

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.

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. 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.

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.

oliver garrett dorchester raid

$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 2021.

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