The Bootleggers’ Trust: Inside Maryland’s Rebellious Prohibition Era

ANNAPOLIS, Md. — After the United States passed the Volstead Act in October 1919, creating a federal enforcement mechanism for Prohibition, most states followed suit with their own enforcement laws.

Maryland did not.

When the manufacture, sale and transportation of intoxicating liquor became illegal nationwide on Jan. 17, 1920, Maryland took an unusual position.

Maryland wasn’t saying that Prohibition wasn’t the law. In fact, Maryland had ratified the 18th Amendment early on. What Maryland refused to do was pass its own state law to enforce it. In effect, Maryland told Washington: Prohibition is federal law; let the federal government enforce it.

And so the federal government did.

Federal agents organized operations throughout Maryland, but enforcing Prohibition in the Old Line State proved challenging. Gov. Albert C. Ritchie, who served from 1920 to 1935, was an outspoken opponent of federal Prohibition enforcement and called its application in Maryland “tyrannical.”

Meanwhile, speakeasies sprang up across the state. Crab houses reportedly became centers for smuggling and illegal drinking. “Look for the sign of the red crab” was one way thirsty customers knew where to find a drink.

Watermen and liquor smuggling also went well together. Chesapeake watermen knew every creek, cove, river and hidden landing along the Bay and tributaries. Federal agents attempting to stop them were entering a labyrinth of waterways that local watermen had spent their lives navigating.

Shortly after enforcement began, various groups, or gangs, sprang up supplying and transporting illicit alcohol. These disjointed groups were in direct competition with each other.

Arrangements to either import or make their own alcohol were handled by these individual groups and, often, they would rat each other out to “eliminate the competition.”

It wasn’t uncommon for rival gangs to steal each other’s shipments, often resulting in shootouts and deaths. One bootlegger who lost a small fortune of booze and several good men to rival gangs shrugged it off as simply “part of the business.”

The Maryland Bootleggers’ Trust

These internal squabbles escalated and began costing gangs huge amounts of money.

At some point in early 1921, just one year after Prohibition began to be enforced, Maryland gangs called a meeting. Where that meeting was held and who attended, we only have anecdotal information.

But the meeting was held at some “back river,” where they discussed cooperation rather than rivalry.

The result of these meetings became known as the Maryland “Bootleggers’ Trust.”

The Trust was remarkably organized. Newspaper accounts described it as having a leader, managers, salesmen, chauffeurs and advisers. It reportedly operated under its own rules and bylaws.

Members were expected to cooperate rather than prey upon one another. If a bootlegger violated the rules, the organization could even retaliate by providing information about him to federal authorities.

The organization also had connections beyond Maryland. Reports claimed Maryland bootleggers were allied with operations in Philadelphia and New York, while experienced bootleggers from the South had also entered the Maryland market.

Bootlegging Comes To Annapolis

One of its more ingenious operations targeted Annapolis.

Young women from Baltimore, Washington, D.C., and surrounding areas were recruited by the Trust to act as intermediaries. The U.S. Naval Academy and St. John’s College became targets.

The women attended social events where they could meet students and quietly supply them with illegal alcohol. Grand jury investigations in Annapolis specifically stated that the women were “in the employ of a trust.”

The operation wasn’t simply a matter of handing a young woman a bottle and sending her to Annapolis.

The women were recruited and transported, and specialized clothing and accessories helped conceal their cargo. Handbags, dresses, flasks and other devices allowed liquor to be carried discreetly into places where a male bootlegger carrying bottles would have attracted considerably more attention.

By 1923, federal authorities were onto the scheme and were trying their best to stop it. Arrests and grand jury investigations connected with women supplying liquor in Annapolis were underway by the spring of that year.

Stopping the women from attending social events and supplying young men with their booze was another matter.

Newspapers had a field day with the phenomenon. One account described the new threat to the supposedly dry college campus as the “dainty liquor pirate wearing high heels and dance frocks, a dimple in her cheek and a saucy twinkle in her eye.”

The strategy also presented authorities with another problem: The Trust hid behind these women, and the college students were unwilling to point fingers.

Even midshipmen apparently weren’t particularly eager to identify the attractive young women who had supplied their hooch. Reports described midshipmen being questioned about where and from whom they had obtained their liquor.

Naval Academy authorities were confronted with smiles instead of answers.

The End Of Prohibition

Prohibition finally ended Dec. 5, 1933, when the nation ratified the 21st Amendment, repealing the 18th Amendment.

For most of those nearly 14 dry years, federal agents in Maryland had contended with bootleggers who became increasingly sophisticated, organized and wealthy.

Members of the Maryland Bootleggers’ Trust must have been disappointed to see Prohibition end. After all, many of them had made fortunes from it.

But … all things must surely come to an end.

To discover more local legends, maritime history and fascinating tales from the region’s past, visit Spooky Solomons Tours at SpookySolomons.com

About The BayNet Expert Series
This article is part of The BayNet Expert Series, which highlights local professionals, historians, nonprofits and community leaders who share their knowledge and expertise with Southern Maryland readers.

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