Cops vs. Bootleggers San Mateo County’s rugged shore kept smugglers a step ahead during Prohibition.

Cops vs. Bootleggers: County’s rugged shore kept smugglers a step ahead during Prohibition

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Like much of the California shoreline, the San Mateo County seaboard was a natural for smugglers. The Coast Guard had difficulty enforcing the National Prohibition Act, which lasted from 1920 to 1933. One steamer, the Ardenza, brought in 25,000 cases of Scotch in 1924 on a voyage that extended from Scotland through the Panama Canal. Most ocean-borne booze, however, came from Canada. Half Moon Bay offered an excellent entry point because of the area’s many landing sites, nearby roads and sparsely populated settlements.

Violent encounters between bootleggers and the authorities were frequent. Author June Morrall recalls one such fight on her website, “Half Moon Bay Memories.”  The Coast Guard boarded a smuggler’s boat near Moss Beach, took the vessel in tow, and left only one sailor to supervise the seized ship. The crooks overpowered him, cut the towline and sped away. The crew on the Coast Guard cutter let go with rifles, machine guns and a deck gun, but the lawbreakers managed to outdistance their pursuers in the dark. The next morning, hatches and wreckage floated ashore, proof that the gunfire had, at the least, hit the fleeing boat.

One of the more interesting coastal remnants of the nation’s dry spell sits near Shelter Cove in Pacifica. There, government agents blasted shut an abandoned railroad tunnel that bootleggers used for a warehouse. Author Barbara VanderWerf recounted the saga of the tunnel in her book, “Montara Mountain.”

At night, rumrunners took over the cove, known then as Smuggler’s Cove, to off-load thousands of bottles of illegal whiskey from Canadian ships. The next day, the whiskey was for sale in San Francisco speakeasies.

“At night, rumrunners took over the cove, known then as Smuggler’s Cove, to off-load thousands of bottles of illegal whiskey from Canadian ships,” she wrote. “The next day, the whiskey was for sale in San Francisco speakeasies.”

The 354-foot-long tunnel was built by the Ocean Shore Railroad, an ill-fated venture designed to link San Francisco with Santa Cruz. The railroad, whose slogan was “Reaches the Beaches,” lasted from 1907 to 1920, when autos increasingly lured away passengers. Faced with continuing mudslides, the company never completed its 75-mile route down the coast.

Speakeasies Were Everywhere

In addition to the railroad tunnel, other reminders remain from the Gatsby age. Mitch Postel, president of the San Mateo County Historical Association, says visitors shouldn’t be surprised.

“On the coastside, at various times, nearly every prominent building served as a speakeasy — even (Pacifica’s) historic Sanchez Adobe,” he says.

Among the most popular haunts today is the lively Moss Beach Distillery, which overlooks the ocean from a cliff that once shielded smugglers. The restaurant boasts a fabled flapper ghost known as “The Blue Lady,” who, some say, wanders the beach in search of her lover. Built in 1927 by Frank Torres, whom Morrall describes as a “Peruvian world traveler,” the establishment was originally dubbed “Frank’s Place.” According to legend, the clientele, said to include mystery writer Dashiell Hammett, was so influential that the place was never raided.

Other spots known for their shady past include the Miramar Beach Restaurant, called the Miramar Hotel during Prohibition. It was designed specifically as a speakeasy, complete with revolving cabinets and other secret compartments for booze. An imposing private residence in Pacifica known today as “Sam’s Castle” was called “Chateau LaFayette,” popular not only for its alcohol but also its restaurant and dance floor. The operators were rumored to be so confident of avoiding arrest that they signaled boats when to bring their illegal cargo ashore.

Hoarders Were the First Targets

Before bootlegging, the era’s main source of liquor was not “rotgut,” but, rather, good stuff stashed by rich people who had planned for Prohibition. Shortly after booze was outlawed, newspapers carried numerous stories about private stocks stolen from homes.

In a research paper in 1978, Eileen Wieland, a student at the College of San Mateo, reported that such thefts occurred almost daily in the early years of Prohibition.  Fame provided no safety shield. Wieland wrote that the San Mateo home of Bank of America founder A.P. Giannini was hit in January 1920 by brazen but disappointed bandits who found only wine. They left a note reading, “We’re looking for booze. We don’t like your vino.”

Still, it was the contraband artists and their customers who stole headlines with colorful tales that were sure to bait news reporters. Take the case, no pun intended, of Jack Mori, who hired an armada of small boats to haul liquor to a dock at what is now Pacifica. In 1921, police confiscated $50,000 worth of alcohol, including 1,000 cases of whiskey, at Mori’s roadhouse.  It constituted one of Prohibition’s richest seizures in the county.

This story first appeared in the September edition of Climate Magazine

Lighthouse keepers had a bird’s-eye panorama of many operations. Jessie Mygrants Davis, daughter of Pigeon Point’s assistant keeper, called the smugglers “quite ruthless men.”

Davis is quoted in “Shipwrecks, Scalawags, and Scavengers: The Storied Waters of Pigeon Point,” by JoAnn Semones of Half Moon Bay. The chronicles include the story of the night Davis’s father, Jesse Mygrants, was forced at gunpoint to drive a band of rumrunners eight miles down the coast.

“They were audacious enough to use the lighthouse derrick to unload their ships,” Davis recalled. “They always came on moonlight nights, so we could see them clearly.”

How Did Prohibition Happen?

Accepting the Republican presidential nomination in 1928, Herbert Hoover said of Prohibition, “Our country has deliberately undertaken a great social and economic experiment, noble in motive and far-reaching in purpose.” If that was true, then San Mateo County could have been considered a laboratory. It had all the ingredients — hijackings, stills, gunfights and speakeasies. In that sense, it reflected much of the nation.

Experiments are supposed to produce answers. To many members of the generations that followed Prohibition, the biggest question was this: How did the United States get to the point that alcohol was outlawed?

The temperance movement stretched back to the early 1800s. But historian Daniel Okrent, author of “Last Call: The Rise and Fall of Prohibition,” believes its ultimate genius was Wayne Wheeler, an attorney and leader of the Anti-Saloon League, founded in 1893 in Oberlin, Ohio. Okrent says Wheeler was able to bring together groups that on the surface seemed directly opposed to one another.

Wheeler’s devotion to the dream of a dry America accommodated any number of unlikely allies. These groups included the Ku Klux Klan.

Writing in Smithsonian Magazine in 2010, Okrent observed, “Wheeler’s devotion to the dream of a dry America accommodated any number of unlikely allies. These groups included the Ku Klux Klan, which joined the radical Industrial Workers of the World in the drive against liquor. The Klan’s anti-liquor sentiment was rooted in its hatred of the immigrant masses in liquor-soaked cities; the IWW believed liquor was a capitalist weapon used to keep the working classes in a stupor. Anti-German hostility in World War I also played a part. A dry Wisconsin politician named John Strange said the ‘worst of all our German enemies … are Pabst, Schlitz, Blatz and Miller.’”

Okrent wrote further that Wheeler’s organization made common cause with social reformers who wanted to wrest political control of cities from forces they thought purchased the immigrant vote through saloons. Suffragists such as Elizabeth Cady Stanton fought not only for a woman’s right to vote, but also, through the temperance movement, sought to prevent the wages of working wives (money that legally belonged to their husbands) from filling the cash registers of corner bars. Prohibitionists also joined racists whose greatest fear, Okrent said, was a black man “with a bottle in one hand and a ballot in the other.”

Who Really Supported Prohibition?

California’s legislature ratified the Eighteenth Amendment in 1919, joining counterparts in every other state except Rhode Island. But popular support may have remained tepid. Gary Kamiya, author of “Cool Gray City of Love: 49 Views of San Francisco,” wrote in the San Francisco Chronicle in 2018 that the City trailed only New York in its wide-open acceptance of unlawful boozing. Kamiya wrote that the Anti-Saloon League “argued falsely” that Californians beyond the San Francisco-centered “whiskey strip” backed Prohibition.

As the Peninsula grew to become a San Francisco suburb during the first two decades of the 1900s, residents may have objected more to drinking establishments than to drinking per se. In 2007, the Redwood City Public Library Archives Committee published “Redwood City: A Hometown History.” In a chapter titled “Saloons, Breweries and Bordellos,” now-retired Redwood City librarian Mary K. Spore-Alhadef explored the county’s quest for respectability.

After the 1906 earthquake, Spore-Alhadef wrote, families began moving south from San Francisco. Many who left behind the City’s highly visible vices brought with them an early version of what later became known as “family values.” As their number grew, Spore-Alhadef said, sentiment “began to turn against the saloon.” Even so, increasingly popular fraternal organizations began to supplant taverns as places where self-described “family men” could indulge in alcohol-fueled conviviality.

It all came crashing down — officially, at least — on January 17, 1920, when Prohibition took effect. The “noble experiment” lasted nearly 14 years until its repeal at 5:32 p.m. on December 5, 1933. At that moment, ready to lift a glass but also weighted by the Great Depression and the nascent threat of Nazism, President Franklin D. Roosevelt summed up the national mood.

“What America needs now,” he said, “is a drink.”