American Tourism & Gambling Could Return to Cuba

By T.D. Thornton

Now that the United States has moved to normalize relations with Cuba, how long will it be until “normal” means a return to tourism, and inevitably, legalized gambling backed by American interests? 

I. Nelson Rose, a California attorney who specializes in international gambling law, told the TDN that based upon an academic research trip he made to Havana two years ago, a safe bet might be seven years. 

Prior to the 1959 revolution and Fidel Castro's subsequent ban on betting, the island nation 90 miles south of Florida enjoyed a reputation as a tropical den of sin where well-to-do Americans gambled and gorged themselves on a bounty of illicit pleasures, many of which were bankrolled and/or operated by U.S. gangsters. 

Among them was Oriental Park, which between 1915 and 1959 served as a magnificent, art-deco gem of Thoroughbred racing in the Havana suburb of Mariano. 

Prior to the establishment of top-level racing in Florida, Oriental Park was the place to see and be seen if you were a fashionable American abroad on winter holiday. 

In its heyday, Cuba's only commercial track drew well-stocked U.S. stables, talented jockeys, and overflow crowds that lined the sloping, palm-lined clubhouse lawn and gardens, as depicted in this vintage newsreel footage. 

But if gambling does return to Cuba, south Florida tracks will have little to worry about in terms of equine competition: Oriental Park's opulent grounds were razed more than 40 years ago. 

A gritty auto parts store and heavy industrial equipment warehouse now occupy the only remaining structures that once housed Oriental Park's lavish open-air clubhouse and sprawling casino. Behind it, the entire one-mile oval and lush infield have been encased in concrete–although the outline of a track is still discernible if you peer long and hard enough at a grainy Google satellite image. 

The sorry state of Oriental Park today belies its colorful history. 

“The track and its surroundings are as fine and commodious as the largest ones in this country,” the New York Times reported upon the track's opening 100 years ago this winter. Four years later, the Times affirmed that the race meet “signalized the beginning of a movement to make Havana a mecca for American sportsmen during the winter months.”

For prohibition-parched Americans in the 1920s, part of the attraction had to do with free-flowing liquor. But the racing quickly prospered because the Cuban government bankrolled ambitious initiatives to import breeding stock. 

At Oriental Park, 2-year-old racing began in January, and entries and results were printed in American newspapers from coast to coast. 

Despite idyllic surroundings, corruption and violence became synonymous with Cuban racing by the 1930s. Like scenes out of an Ernest Hemingway novel, gunfire mingled with mariachi music near the betting ring. 

It was an open secret that when track-backed bookmakers thought they were going to lose money on a heavily bet horse, they would call up to the stewards' stand. Using a system nicknamed “window washing,” the stewards would raise and lower a window shade corresponding to the number of the horse they wanted “protected.” It was the starter's job to watch for this signal, and to make sure the hot horse was at a disadvantage when the starting tape sprang up. 

“The problem was partly the Depression–crooked stewards, races fixed, horses that were hyped or nobbled,” wrote Robert Lacey in his book, Little Man: Meyer Lansky and the Gangster Life. “American owners were becoming less and less inclined to risk their better Thoroughbreds on the sea voyage to Havana, while no sensible bettor would chance his money with the track's bookies.” 

In the 1940s, president Fulgencio Batista reached out to Lansky to help grow Cuba's gambling sector. Despite deep racketeering ties, Lansky believed the best way to boost business was to run squeaky-clean betting operations, so he outsourced the overhaul of Oriental Park to Rockingham Park founder Lou Smith. Paradoxically, even as the Batista regime grew increasingly corrupt, the actual races became better policed, and the betting product flourished. 

By the early 1950s, top U.S. jockeys routinely ventured to Cuba to gain late-December victories while chasing winningest rider titles. Movie stars like Kirk Douglas and Rita Hayworth were listed in society pages as Oriental Park guests, and the Harlem Globetrotters basketball team even made a group appearance. 

New York investors took over, and by 1956 the track was boasting record business. 

But greed led to the downfall of gambling on the island. Then Cuba as a whole disintegrated into chaos. 

“American and Cuban mob families opened luxurious casino resorts, each one bigger and more successful than the last,” Rose wrote in an online essay titled Cuba Will Have Casinos, Again. “The money poured in. Batista got a cut of everything. Still, most Cubans never shared the wealth they saw all around them, and corruption was rampant. The result was revolution.” 

Amid the violence of the 1959 New Year's Day revolt, Batista fled the country. So too did American racing executives. Angry crowds destroyed gaming tables and turned loose swine inside the island's ritzy casinos. 

Most online sources today claim that racing ceased at Oriental Park after the 1959 revolution. But this is not so–it's just that the track's history has been extremely difficult to document since the U.S. Government cut off relations with the Castro regime in 1961. 

According to the Times, a group of horsemen salvaged the 1959 spring meet, running an abbreviated season in “strangely quiet” surroundings with limited betting. 

Castro soon banned wagering and commandeered the track to be run by Cuba's National Institute for Sport. By 1964, the plan was for tourists from Soviet bloc nations to keep the sport alive as a pastime. Racetrack attendance dwindled even as crowds of 40,000 packed nearby ballparks to watch “socialist baseball.” 

By the mid-1960s, any Thoroughbreds of value had been surreptitiously sold off the island to turn illicit profits. According to one Cuban cultural website, the rest were transferred to a two-furlong bush track in Wajay, south of Havana, were clandestine betting presumably took place against socialist strictures. 

When Oriental Park ceased racing for good in 1967, every scrap of tack and furniture was scavenged for other purposes. The main clubhouse portico initially housed a movie theater. Other buildings were torn down or converted to ramshackle stores. 

Rose has been predicting the re-emergence of gambling in Cuba since 2009. 

“Prior to island-based casinos, the first new wave would be cruise ships docking in Cuba's territorial waters,” Rose said. “Obviously the U.S. would be such an enormous market for them. Cuba is absolutely desperate for whatever it can raise, and gambling is always seen as a painless tax, especially if the only people who can participate are foreigners.” 

Unlike Oriental Park, Rose said many of the casinos are still “frozen in time.” He said he actually took in a variety act at the still-functioning Tropicana showroom–although he described the performance as dated as the dust on the chandeliers.

Rose said that the former gambling halls he toured seem small by today's standards. But, he explained, even in the early days of Las Vegas, casinos went for a more intimate feel before expanding to “slot warehouses.” 

Rose said a few of the hotels still function as lodging establishments. Many have been converted to apartments. 

“The interesting thing is the buildings are still there and the casinos are still there, except there is no actual gambling going on in Cuba,” Rose said. “No one has any money.”