Shadowland was San Antonio’s casino and underground bar during the Prohibition era


You’ve probably written a column on Shadowland before, but I’ve always been curious about its history during Prohibition and WWII.

Although this legendary Texas truck stop lasted over 30 years, the elements that define it all came together at the start: high quality jazz, dancing to live music, dinner and a floor show and the experience of driving to what seemed like the middle of nowhere to enter a fantasy world of fantasy environments and vaguely illicit events.

Under the name “Shadowland Dinner Club”, it opened in March 1927, more than seven years after Prohibition entered into force on January 17, 1920, banning the production and consumption of alcoholic beverages until its release. repeal. The nightclub was advertised in local newspapers as “Texas’ coolest place to dine and dance,” with an emphasis on its chicken and steak dinners, dancing to the Troy Jazz Band Floyd “every night from 8 pm to 3 am” and a show of “song, dance and novelty numbers, brought in from the big cities” and changed weekly.

Dinner costs $ 1.25 to $ 1.50. The cover charge to see the show was $ 1, which you didn’t have to pay if you didn’t stay after 10pm. Even then, it was more expensive than a counter meal or a movie, but not especially. – because Shadowland didn’t make its money on the chicken, the steak, or the shows.

The Troy Floyd Orchestra was a staple of the first Shadowland Dinner Club in the 1920s.


In the charter filed earlier that year by a union of five investors, the remote business was supposed to become something like a country club, for the encouragement of sports such as tennis and wrestling. Chief among the partners was Earl Ramsey, who operated the Southern Club at 121½ Soledad St., one of San Antonio’s hottest gambling dens. Shadowlands was going to be the hottest gambling house outside of town.

Built for $ 75,000, it wouldn’t be in a basement or alleyway. In fact, he wouldn’t have a mailing address at all. In advertisements, promotional materials, legal documents and newspaper articles, Shadowland was always “10 miles from Blanco Road, well beyond the city limits and beyond the reach or interest of city ​​and law enforcement ordinances.

“Located in a forest,” as described in a San Antonio Express infomercial on June 21, 1927, the club was “conveniently located… just far enough out of town for a pleasant stroll that would whet my appetite”. An arrow-shaped sign read, rather ominously, “To The Shadowland.” A long gravel driveway led to the hexagonal building preceded by an extended porte-cochere where customers abandoned their cars to the unusual luxury of valet parking.

The dining room had the dance floor and the stage. It was filled with round tables with white tablecloths and rattan chairs with matching tiebacks. Above was a mirror ball chandelier, six feet in diameter, which rotated at the start of the dance. The multicolored reflections and the changing light gave the club its name and its otherworldly atmosphere. Next to the great hall were a few smaller spaces for roulette wheels, blackjack tables, and dice games.

“When the house was lucky we would win $ 20,000 a night on the two crappy tables, roulette and the game of blackjack,” Ramsey told the San Antonio Light for a story that was published on December 5, 1962. Less often, when a player has drawn a big hand, Shadowland could lose just as much. The big players’ dinners were paid for and they were given a pass to enter the club instead of paying their entry.

The first time the club was raided, the game was just a footnote. (Club owners would attest that the people in the arcades were “just visiting”, not for the money.)

Photos of the Shadowland Dinner Club, including a Federal Raid Closure Notice, in UTSA Special Collections.

Photos of the Shadowland Dinner Club, including a Federal Raid Closure Notice, in UTSA Special Collections.


Acting on the advice of the Women’s Christian Temperance Union, local federal agents made an example of the club, which they visited incognito about fifty times from May to July 1927, during a “war on alcohol” highly publicized. By the time of the raid on August 6, 1927, they understood how the place operated. Trusted regulars might mark a bottle of something alcoholic from an outside porter. Others could wait to be seated, order ginger ale and ice cream, and get the rest from staff moving around the room, asking customers if they had everything they needed.

One wonders if Shadowland could provide. During the seemingly nonchalant raid, staff told guests to stop drinking and held out a box to empty their unfinished bottles, to remove and pour on the floor. Some 35 bottles, entered into evidence in the subsequent hearing in United States District Court, contained a smelly assortment – apricot and peach brandy, Chianti and port, gin, tequila, whiskey, an “unnamed liquid” and an antiseptic.

For selling illegal alcohol by the bottle and trying to destroy evidence, the owners of Shadowland were among the first of 20 establishments to close their premises. The doors to the club were padlocked and the windows were boarded up… for a year.

The excellent house group, led by Troy Floyd and including trumpeter Don Albert, went to the Plaza Hotel and recorded “Shadowland Blues” on the Okeh label (available on YouTube). There is no mention of the eponymous club in the lyrics. When Shadowland reopened in October 1928, most of the band came together under the name Don Albert and his Ten Pals. Albert, a respected jazz musician here and in New Orleans, would call the place “the Southwest’s first major nightclub”, giving credit to the advertising slogan, “The South’s Leading Nightclub”.

With the reopening, a new direction came under the leadership of veteran club operator Bill Cohen, who bought Shadowland about a year later. But it was business as usual. Despite the stock market crash of 1929 and the ensuing economic crisis, Cohen told the Light that with little competition, “we are running a very successful club.” Many people would “put a little money on the table, in the hope of making it a panacea for their difficulties.”

During the four public holidays in March 1933, Cohen operated a check cashing business that allowed club goers frustrated with lack of access to their funds during the shutdown. It worked so well for the house – funding the bets of the temporarily cash poor – that Shadowland continued the service. With part of the profits, the club installed a new dance floor, an outdoor dining area and a cooling system.

Law enforcement was inconsistent, but the club was raided again, this time by the Texas Rangers who ransacked playing equipment. When it reopened six months later, Shadowland bowed to the Depression by operating only three evenings a week and halving the price of admission. A new cook introduced the charcoal grilled steaks, a novelty at the time that drew the curious to try it. Broadcasts on WOAI radio promoted club acts, such as the Ben Bernie and Vincent Lopez orchestras.

Cohen brought Shadowland through the Depression. “The authorities would let us operate for a while and then arrest us,” he noted. In 1941, along with other irons in the fire here and in Fort Worth, he sold shares to two new partners, including conductor Dude Skiles, who made the club his home port. During World War II, with the rationing of gasoline and food, getting to Shadowland was more difficult. A defense stamp dance, where gate receipts benefited the war effort, does not appear to have been repeated.

At the start of the war, Shadowland seemed to function more like an after-hours club, for soldiers and their dates who had spent the evening in the rooftop garden of a downtown hotel and traveled 10 miles. “on Blanco Road” to continue the party. . As the war and decade drew to a close, Shadowland turned more to private parties – club, lodge, and military unit events.

Cohen and Skiles sold in 1949 to Cookie and Bill McKinney, who made it into what may have been the first San Antonio bottle club to circumvent Texas law banning the sale of alcohol by drink. The McKinneys stuck to the restoration and abandoned the game. Shadowland once again became a dance hall open to all when conductor Larry Herman and his wife Merijeanne bought it in 1961, after having it. praised a few times for their “Over 29 Club” performances. The Hermans renamed it Roaring 20s, after the club’s original heyday, and brought in jazz greats – including Louis Armstrong, Count Basie, Tommy Dorsey, Harry James and Glenn Miller – for an audience. nostalgic until the club closed in 1998.

LITERARY FAIR: The Boerne Book and Arts Festival will take place from 10:00 a.m. to 4:30 p.m. Saturday in Boerne’s main square, featuring presenters with connections to San Antonio and an interest in our history. Charlotte Kahl, Founder of the Old Spanish Trail Centennial Celebration, and David L. Peche, Author of “Downtown San Antonio”, will speak at the “Early Roads and the Old Spanish Trail” panel discussion; and Bruce Shackleford, curator of Texas history at the Witte Museum and contributor to “King Ranch: A Legacy in Art”, will participate in a “Texas Ranches and Texas Rangers” panel. This columnist will host a panel on “Heroines of World War II” with authors Katherine Sharp Landdeck (“Women with Silver Wings”), Patricia Portales (contributor to “Latina / os and World War II”) and Cindy Weigand (editor, “Women of Texas in World War II.”)

All events are free and open to the public. A full schedule is at www.boernebookfest.

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