Prohibition - “The Roaring Twenties”

Whiskey Bandits:

With Prohibition, a new breed of thieves – the whiskey bandits – began targeting caches of whiskey.  Over the Christmas holiday in 1919, the Versailles Road farm of H. J. Schlesinger was raided of twenty cases of whiskey from its cellar.  He was the son in law of R. S. Strader, a whiskey broker in Lexington.  The next month, Castleton Farm was also raided by bandits who liberated another twenty cases from its wine cellar.  The thieves left one case, with a note that read, “mark of their appreciation for the opportunity given them to take away that which was to them more valuable than jewels.”[i]

Old Tarr Distillery, circa 1900

Old Tarr Distillery Raid:

On the night of March 20, 1920, a band of masked whiskey bandits raided the warehouses at the William Tarr & Company, on Manchester Street.  After overpowering the two guards, the thieves took ninety-six cases of bonded whiskey from the government storeroom.  The whiskey was valued at $20,000.

After this raid, the remaining seventy-six barrels of Old Tarr bourbon were removed in April 1920 to the concentration warehouses in Louisville.  The newspaper indicated that the value of this bourbon was $266,000.[ii]

Pepper Distillery, circa 1900

Pepper Distillery Raid:

On the winter night of December 2, 1920, whiskey bandits struck the bonded warehouses at the Pepper distillery.  That night William Anderson, a revenue agent, and William Nix, a distillery guard, were making their rounds as usual checking on the warehouses.  At the time, eleven thousand barrels and eighteen thousand cases of bottled bourbon were still stored in the warehouses.

About 1:30 am, the guards were rushed by a band of ten to twelve bandits hiding on the bank of the Town Branch, near the last warehouse.  Agent Anderson ordered the thieves to stop and fired a shot from his revolver.  The band of thieves immediately returned fire and killed Agent Anderson.  Guard Nix was chased toward the office, but escaped and raised the alarm.  The thieves left the area, before the police arrived from Lexington.  Witnesses stated that two touring cars and a truck, running without lights, raced out Old Frankfort Pike at about two o’clock.  The next morning the warehouse wall was “peppered” with holes from the battle.

The distillery increased the security to nine guards and the revenue service sent two more agents.  These guards patrolled the grounds for the next several months, with loaded shotguns and revolvers at the ready.

The Governor offered a reward of $300 for the capture of the thieves.  Rumors stated that organized crime from Chicago was behind this raid.  The bandits were never found.  This is the first attempt to steal whiskey from the facility.  However, several weeks before one of the guards was questioned about the whiskey stored in the warehouses and offered, “how would $6,000 look to you.”


The first arrest of illegally selling whiskey in Lexington occurred on the first day of Prohibition, when Anna Wilson was arrested for selling a quart of whiskey to Charles Cohen.  She was arrested by Deputy Agent U. G. McFarland.  She was later released on three hundred dollars bond.[iii]

The Jungle District:

Bootlegging activities became concentrated around Fifth and Smith Streets, which became known locally as the “Jungle”.  Bootleggers would openly solicit passersby - “buy a pint from me, boss” –a pint of moonshine sold for $2.  Several shootings occurred between rival bootleggers.  The police began to send in undercover patrolmen into the jungle to fight the “booze traffic.”

On the night of January 16, 1927, Patrolmen J. J. Estes and Merritt Oliver, in plain clothes, were assigned to the jungle to buy liquor.  After making two arrests, they returned to the district around 9:30 pm and were approached by Richard Carr, on Kenton Street.  After buying a pint from Carr, the officers attempted to arrest him.  However, Carr broke free and fled down Kenton.  He paused to fire a shot at the pursuing officers, seriously wounding Estes, before disappearing in the darkness.  Estes was taken the hospital, where he died two days later.

Meanwhile, Carr was quickly caught at a rooming house on Grant Street and confessed.  Later, it was discovered that he was under indictment for highway robbery and had just been convicted of three count of violation of Prohibition laws.

After Patrolman Estes’ death, J. Morgan Gentry, Commissioner of Public Safety, told the public that “the police department will do all that can be done to eradicate what seems to be a nest of bootleggers.”[iv]

One of the more interesting local bootlegging cases and was known as the “Dishwater Case.”  When agents raided the home of Hugh and Mary Mason, in January 1930, she poured the whiskey into dishwater before the agents could seize the evidence.  Both were charged with possession of liquor.  After smelling the dishwater, the jurors found her guilty.  She was given a suspended sentence.[v]

Two young moonshiners arrested slightly before Prohibition in Fayette County by U. S. Marshall.

Illegal Stills:

Prior to Prohibition, a quart of quality bourbon sold for between a dollar and a dollar and a quarter, with roughly two thirds of that amount paying excise taxes.  In Eastern Kentucky, a cottage industry developed to distill moonshine to avoid paying excise taxes.  By adding caramelized brown sugar and shoe polish to their white whiskey, these moonshiners were reputed to be some of the best distillers.  After Prohibition, the price of a pint of quality whiskey was three to four dollars.  Needless to say, the increased profitability led to an increase in the number of illicit stills.

On February 18, 1920, the first still was discovered on North Limestone, when Federal agents seized a 7-gallon still and 10-gallons of mash.  Pete Metrotus was arrested and charged with possession of a still and distilling apparatus and using the same for unlawful manufacture of alcoholic liquor.[vi]

Illegal Stills, near Lexington

Lexington Brewing Company:

The Lexington Brewing Company was located on the south side of Main Street, opposite DeWeese Street.  With the onset of Prohibition, the company officially ceased beer production and only produced legal beverages, with low alcohol content.  The firm received a federal permit to manufacture non-intoxicating beverages.  The brewery was classified as a de-alcoholing plant and was authorized to produce beer, with less than one-half of one percent alcohol.

During March 1919, John Kloecker, John J. Galvin, Thomas C. Bradley, James T. Looney and James P. Kearns acquired the Lexington Brewing Company[vii]  Kloecker was the brewing company's Secretary and Treasurer, Galvin was a local beer distributor, Bradley was the Mayor of Lexington in the 1920s (and was involved with the Kentucky Association Racetrack, Phoenix Hotel and Guaranty Bank & Trust Company), Looney was one of the city's larger grocers and Kearns was the City's Assessor.

However, the brewery continued to brew real beer in defiance of the law.  For some reason, local officials failed to note a brewery operating on Main Street, with railcars and trucks coming at all times.  Apparently, the influence of the brewery's owners (including the former mayor) convinced local officials to overlook these illegal activities.

However, Sam Collins, newly appointed director of Prohibition for Kentucky, had taken notice of these activities.  Months earlier, Collins had arrested Cincinnati's George Remus, lawyer turned King of the Bootleggers.  After his arrest, Mr. Remus was quoted that he knew of only two officials who refused a bribe.  Agent Collins was one of them.  He had been offered $100,000 to quit the Treasury's Prohibition Bureau.  At the time, his salary was only $4,600 annually.[viii]

In May 1922, federal prohibition agents from Louisville searched a railroad car at the brewery's siding for illegal beer, but found only legal beer.[ix]  After this search, Agent Collins continued to watch the brewery.

Lexington Brewing Company, circa 1900

On June 2, 1922, prohibition agents again raided the Lexington Brewing Company after one of its trucks, loaded with "high proof" beer, was seized.  Agent B. F. Unthank testified later that he had received a "tip" that beer was being delivered from the brewery on certain dates.  From a rented room across the street in the Lynx Hotel, Agent Unthank observed a truck loaded with barrels leaving the brewery and then followed the truck to a soft drink stand owned by John Furlong, on North Limestone.  The barrels were observed being unloaded from the brewery's truck and taken inside the store.

The truck returned to the brewery and was again observed being loaded with barrels.  Director Collins and Agent Unthank then followed the truck to the Otto E. Fisher soft drink stand, also on North Limestone.  At about five o'clock in the afternoon, when the truck stopped in the alleyway, the "dry" agents seized the truck and arrested the driver, Charles Wickline, and his assistant, Joe Dotson.

The agents drove the truck back to the Federal Building where it was inspected.  They discovered fifteen barrels of beer, each containing one hundred bottles of "high proof" beer packed in sawdust.  Shortly after seven o’clock, a force of prohibition agents raided two soft drink stands on North Limestone.  These raids led to the seizure of ten barrels of beer from H. C. Lancaster & Brothers and seventeen barrels from John Furlong.  No arrests were made until the contents of these barrels could be tested.  The agents then searched the brewery's plant and bottling house for over an hour and a half, turning up another fifty barrels of beer.[x]

During the next month, newspaper headlines were full of details of the largest Prohibition seizure in Kentucky.  These headlines included "5,000 Bottles of Beer Taken in Raid," "Collins Cites Lexington Brewing Co As A Result of Beer Seizure," "Contents of Over 5,000 Bottles of Beer Poured Into Sewer" and "U. S. Jury Returns True Bill Result of Big Beer Seizure."

On June 7, Agent Collins instituted legal proceedings against the Lexington Brewing Company to revoke its federal permit to manufacture non-intoxicating beverages (near beer).  A hearing was scheduled for June 23.[xi]

After the seizures, the beer was stored in the basement vault at the U. S. Post Office building.  During the next few days, several hundred bottles mysteriously disappeared from the federal vault.  After the discovery of this liberation, Agent Collins ordered the remaining beer destroyed by pouring the contents into the city drains.  On Saturday, June 11, pedestrians walking along Main Street noticed a river of beer flowing into the city's sewers from the Post Office, where the prohibition agents spent a full day pouring out 5,724 bottles of beer.  Two bottles from each barrel were retained as evidence.[xii]

The next week, the federal grand jury returned criminal charges against six officers and employees of the Lexington Brewing Company and the four soft drink stand owners.  The six included John Kloecker, John J. Galvin, Theodore Lassig (brew master), John Skain (foreman), Charles Wickline (truck driver) and Joe Dotson (helper).  Brewery owners Mayor Bradley, Assessor Kearns and Grocer Looney were not charged.

The criminal charges contained twelve counts alleging the manufacturing and sale of high proof beer.  The first count charged the company's officers with "willfully, unlawfully and feloniously" conspiring to commit an offense against the United States through the manufacture of certain intoxicating liquors, "namely 100 barrels of bottled beer, containing one hundred bottles each."  The second count accused the company with conspiring to sell the beer, the third count with the actual making of the beer and the fourth, fifth, sixth and seventh with selling it.  The eighth count alleged possession of 100 barrels of beer at the brewery for purposes of sale as a beverage.  While the ninth, tenth, eleventh and twelfth counts charged them with transporting the beer to the soft drink stands.[xiii]

The six officers and employees pleaded not guilty the next day at their arraignment and were released on bonds of $2,000 each.  Mr. Kloecker posted all six bonds.  The soft drink merchants were released on $500 bonds.[xiv]  Judge A. M. J. Cochran scheduled the criminal trial against the six defendants to begin July 10.[xv]  However, before the trial started, the case was postponed until the first term of federal court in January 1923.[xvi]

After the continuance of the criminal case, on August 1, 1922, Agent Collins held a hearing to revoke the company's federal permit.  At the hearing federal agents testified about the raid and the contents of the "high proof" beer.  John Furlong testified that he had no knowledge of any real beer being delivered to him by the brewing company.  He indicated that he purchased two quantities - one for $10.50 a barrel and a "special" for $15.00 a barrel.  These barrels contained unlabeled black bottles of beer.  The attorneys for the brewing company offered no evidence at this hearing.

At the close of the hearing, Agent Collins forwarded the information to Washington for action.[xvii]  Subsequently, the company's federal liquor permit was revoked.

On January 10, 1923, the six brewery employees entered guilty pleas in federal court.  The defendants were allowed to execute new bonds for their appearances at a later date when they were to be sentenced.  Judge Cochran issued a temporary restraining order enjoining the defendants from manufacturing, selling or possessing intoxicating liquors.  The U. S. Attorney also requested that the brewery property be closed for a one-year period.[xviii]

In December 1930, Prohibition agents raided a house on East High Street and found a copper still, 200-gallons of mash and 6-gallons of whiskey.  E. W. Bryant was arrested.  The house was owned by the Lexington Board of Education.[xix]

Whiskey Runners:

With the remoteness of Eastern Kentucky, a number of bootleggers setup their stills in the valleys and hollows to avoid detection.  The bootleggers sold their products to whiskey runners, who brought the whiskey into the major cities.  The whiskey runners rebuilt their cars to look normal (“stock”) from the outside, but installed supercharged engines under the hood.  The interior was stripped and racks were installed to hold their whiskey.  Then in the middle of the night, the runners would head towards Lexington.  Many used Paris Pike, Russell Cave Road or Winchester Pike.  Paris Pike was famous for Dead Man’s Curve, near the county line, where a number of fatal accidents had occurred.

The Federal agents began staking out the routes and stopping suspicious cars.  Instead of stopping, many runners ran from the agents, which led to a number of exciting high speed chases.  Sometimes, the runners won and sometimes the agents won.  Another tactic of the agents, was to wait until the runner stopped to deliver his whiskey and arrest the delivery man.

In April 1930, 108-gallons of first-grade Tennessee corn whiskey was seized on Richmond Road, when Federal agents stopped a Cadillac Touring Car.  Two men were arrested and the car seized.  The whiskey was headed for the spring race met at the Kentucky Race Track.[xx]

On Thursday night, August 14, 1930, Federal agents blockaded several roads into Lexington, based upon a tip that a Package Straight Eight Closed Car was running whiskey into Lexington.  Two agents, Albert Randsell and Ludlow Cook, were looking out the window of their office, in the Post Office on Main Street, when the spotted the whiskey runner’s car driving north on Walnut Street.  The two agents jumped in their car and gave chase out Paris Pike.  They stopped the car at Dead Man’s curve and arrested the driver.  In December, Alex C. Ray was finally arrested after a high speed chase out Russell Cave Pike, from downtown.  The chase lasted 9 miles.  In Ray’s roadster was 5-gallons of moonshine whiskey.[xxi]


[i] Lexington Herald, January 17, 1920, page 7, column 2.

[ii] Lexington Herald, April 6, 1920, page 10, column 2.

[iii] Lexington Herald, January 18, 1920, page 1, column 4.

[iv] Lexington Herald, January 17, 1927, page 1, column 8, January 18, 1927, page 1, column  and January 19, 1927, page 1, column 6 – 7 and Lexington Leaders, January 17, 1927, page 1, column 1, January 18, 1927, page 1, column 5 and January 19, 1927, page 1, column 2.

[v] Lexington Leader, January 18, 1930, page 1, column 5.

[vi] Lexington Leader, February 18, 1920, page 1, column 1.

[vii]  Herald, March 16, 1919, page 3, column 2.

[viii]  Prohibition, Edward Behr, Arcade Publishing, New York, 1996, page 104, 1126-7.

[ix]  Lexington Herald, June 3, 1922, page 1, column 8.

[x]  Lexington Herald, June 3, 1922, page 1, column 8, June 4, 1922, page 1, column 4 and June 4, 1922, page 1, column 1 and Leader, June 3, 1922, page 1, column 8.

[xi] Lexington Leader, June 7, 1922, page 1, column 8 and Lexington Herald, June 8, 1922, page 1 and 7.

[xii] Lexington Leader, June 11, 1922, page 1, column 1 and Lexington Herald, June 11, 1922, page 1, column 3.

[xiii] Lexington Leader, June 14, 1922, page 1, column 7 & 8 and Lexington Herald, June 15, 1922, page 1, column 1.

[xiv] Lexington Leader, June 15, 1922, page 1, column 1 and Lexington Herald, June 16, 1922, page 1, column 3.

[xv] Lexington Herald, June 17, 1922, page 1, column 4.

[xvi] Lexington Leader, July 10, 1922, page 1, column 2 and Lexington Herald, July 11, 1922, page 1, column 2.

[xvii] Lexington Leader, July 19, 1922, page 1, column 4, July 28, 1922, page 1, column 3, August 1, 1922, page 2, column 4, and August 2, 1922, page 3, column 1 and Lexington Herald, August 1, 1922, page 1, column 2 and August 2, 1922, page 1, column 3.

[xviii] Lexington Leader, January 10, 1923, page 1, column 5 and Lexington Herald, January 11, 1923, page 1, column 5.

[xix] Lexington Leader, December 14, 1930, page 1, column 1.

[xx] Lexington Leader, April 16, 1930, page 1, column 4-5.

[xxi] Lexington Leader, August 15, 1930, page 1, column 5 and December 3, 1930, page 1, column 6.

William M. Ambrose. Bluegrass Prohibition, Limestone Press, Lexington, 2007.