Prohibition-era S.A. casino boasted great jazz

You’ve probably already written a column on Shadowland, but I’ve always been curious about its history during Prohibition and World War II.

— Bradford Breuer Although this legendary Texas roadhouse lasted more than 30 years, the elements that defined it all came together at the beginning: 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 fancy surroundings and vaguely illicit goings-on.

As “Shadowland Dinner

Club,” it opened in March 1927, more than seven years after Prohibition took effect on Jan. 17, 1920, outlawing the production and consumption of alcoholic beverages until its repeal. The nightclub was advertised in local newspapers as “the coolest place in Texas to dine and dance,” with the emphasis on its chicken and steak dinners, dancing to Troy Floyd’s jazz orchestra “every night from 8 p.m. to 3 a.m.” and a show of “singing, dancing and novelty numbers, brought from the larger cities” and changed weekly.

Dinner cost $1.25 to $1.50. The cover charge to see the show was $1, which you didn’t have to pay if you weren’t going to stay past 10 p.m. Even then, that was more expensive than a lunchcounter meal or a movie, but not especially so — because Shadowland didn’t make its money on chicken, steak or shows.

In the charter filed earlier that year by a syndicate 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 the most fashionable gambling houses in San Antonio. Shadowlands was going to be the most fashionable gambling house outside the city.

Built for $75,000, it wouldn’t be in a basement or a back street. In fact, it wouldn’t have a street address at all. In ads, promotional materials, legal documents and newspaper stories, Shadowland was always “10 miles out Blanco Road, well beyond the city limits, and beyond the reach or interest of city ordinances and law enforcement.

“Set in a woodland,” as described in a San Antonio Express advertorial on June 21, 1927, the club was “advantageously located … just far enough from the city for an enjoyable ride to whet the appetite.” An arrowshape sign pointed, rather ominously, “To The Shadowland.” A long gravel drive led to the hexagonal building fronted by an extended porte-cochere where guests surrendered their car to the unusual luxury of valet parking.

The dining room had the dance floor and stage. It was filled with round tables with white cloths and cane chairs covered in matching tie-backs. Above was a mirror-ball chandelier, six feet in diameter, set spinning when the dancing started. The multicolor reflections and shifting light gave the club its name and its otherworldly atmosphere. Off the big room were a few smaller spaces for roulette wheels, blackjack tables and dice games.

“When the house was lucky, we’d make $20,000 a night on the two crap tables, the roulette wheel and the blackjack game,” Ramsey told the San Antonio Light for a story that ran Dec. 5, 1962. Less often, when a player drew a big hand, Shadowland could lose just as much. High rollers’ dinners were comped, and they received a pass to enter the club instead of paying their way in.

The first time the club was raided, the gambling was just a footnote. (Club owners would testify that the people in the gaming rooms were “just visiting,” not playing for money.)

Acting on tips from the Women’s Christian Temperance Union, local federal agents made an example of the club, which they visited incognito an impressive 50 times from May through July 1927, during a much-ballyhooed “war on alcohol.” By the time of the raid, Aug. 6, 1927, they understood how the place worked. Trusted habitues could score a bottle of something alcoholic from a porter outside. Others could wait until seated, order ginger ale and ice and procure the rest from staff moving about the room asking customers if they had everything they needed.

It’s debatable whether Shadowland could provide. During the seemingly lackadaisical raid, staff told guests to stop drinking and held out a box to dump their unfinished bottles, to be taken out back and poured on the ground. Some 35 bottles, entered into evidence at the subsequent hearing in U.S. district court, contained a queasy assortment — apricot and peach brandy, Chianti and port wine, gin, tequila, whiskey, an “unnamed fluid” and an antiseptic.

For selling illegal liquor by the bottle and attempting to destroy evidence, Shadowland’s owners were among the first of 20 establishments to have their premises closed. The club’s doors were padlocked, and the windows were boarded up … for one year.

The excellent house band, fronted 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’s no mention of the eponymous club in the lyrics. When Shadowland reopened in October 1928, most of the band got back together as Don Albert and his Ten Pals. Albert, a respected jazz musician here and in New Orleans, would call the place “the first important nightclub in the Southwest,” giving credence to the ad slogan, “The South’s Leading Nightclub.”

With the reopening came new management under 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 resulting economic crisis, Cohen told the Light that with little competition, “we operated a very prosperous club.” Many people “would take a little money to the table, hoping to run it into a cure-all to their difficulties.”

During the four-day Bank Holiday of March 1933, Cohen operated a check-cashing business

that enabled clubgoers frustrated by lack of access to their funds during the shutdown. It worked so well for the house — financing bets from the temporarily cash-poor — that Shadowland continued the service. With some of the profits, the club put in a new dance floor, an outdoor dining area and a cooling system.

Enforcement was inconsistent, but the club got raided again, this time by Texas Rangers who trashed the gambling equipment. When it reopened six months later, Shadowland bowed to the Depression by operating only three nights a week and cutting the admission price in half. A new cook introduced charcoal-broiled steaks, a novelty at the time that drew the curious out to try it. Broadcasts on WOAI radio promoted the club’s name acts, such as the orchestras of Ben Bernie and Vincent Lopez.

Cohen got Shadowland through the Depression. “The authorities would let us operate for a while, then shut us down,” he noted. In 1941, with other irons in the fire here and in Fort Worth, he sold shares to two new partners, one of whom was orchestra leader Dude Skiles, who made the club his home base. Through World War II, with gasoline and food rationing, driving out to Shadowland was more difficult. A Defense Stamp dance, where door receipts benefitted the war effort, seems not to have been repeated.

In the early days of the war, Shadowland seemed to operate more like an after-hours club, for soldiers and their dates who had spent the evening at a downtown hotel roof garden and went 10 miles “out Blanco Road” to keep the party going. As the war and decade wound down, Shadowland turned more to private parties — club, lodge and military unit events.

Cohen and Skiles sold out in 1949 to Cookie and Bill McKinney, who turned it into what may have been San Antonio’s first bottle club to get around the Texas law against selling liquor by the drink. The McKinneys stuck with catering and ditched the gambling. Shadowland came back as a dance palace open to all when bandleader Larry Herman and his wife Merijeanne bought it in 1961, after leasing it a few times for their “Over 29 Club” performances. The Hermans renamed it the 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 nostalgic audiences until the club closed in 1998.

LITERARY FAIR: The Boerne Book and Arts Festival will take place from 10 a.m. to 4:30 p.m., Saturday in Boerne’s Main Plaza, showcasing some presenters with San Antonio connections 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 on the “Early Roads and the Old Spanish Trail” panel discussion; and Bruce Shackleford, Texas history curator at the Witte Museum and contributor to “King Ranch: A Legacy in Art,” will take part in a “Texas Ranches and Texas Rangers” panel. This columnist will moderate a panel on “Heroines of World War II” with authors Katherine Sharp Landdeck

(”The Women with Silver Wings”), Patricia Portales (contributor to “Latina/os and World War II”) and Cindy Weigand (editor, “Texas Women in World War II.”)

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

/ A 1928 advertisement in the San Antonio Light touted the legendary speakeasy “10 miles out on the Blanco Road.”