Three hours out of the Florida Keys, within wading distance of Cuba’s north-central coast, a 28-foot speedboat slowed, its pilot cut the engine, and the sleek hull slid silently to a stop on an ink black sea.
Rain squalls had passed, but a trailing band of storm clouds lingered, hiding the moon -- perfect cover for the night’s illicit mission: smuggling.
The unusual contraband loaded aboard that night in 2004 wasn’t dope; it wasn’t even the typical, ragtag human cargo of desperate asylum seekers. But the value of even a small boatload of the smuggled goods could run into the millions of dollars.
On Big Pine Key, a three-hour high-speed cruise across the Florida Straits, Ysbel Santos-Medina waited to take delivery along a stretch of beach about 30 miles north of Key West. The former truck driver and small-time drug trafficker, a mastermind of smuggling logistics, had arranged everything. His last responsibility would be forwarding the goods to California.
Medina’s contraband on that summer night represented the latest thing in Caribbean region smuggling -- five Cuban baseball players.
Today, top pitchers and shortstops have surpassed dope, rum and tobacco as the commodities of choice for traffickers working the old Spanish Main.
Each of the smuggled ballplayers -- former stars of domestic Cuban teams -- arrived in the U.S. hoping to follow in the cleat marks of previous defectors such as pitcher Orlando “El Duque” Hernandez of the New York Mets.
Their crossing that night was financed, according to court documents and testimony, with payments totaling $225,000 by an Encino sports agent who would become the first agent ever convicted on federal charges of smuggling athletes.
But this was no isolated episode. Since 2000, about 40 other Cuban players have been spirited out of the island nation on similar smuggling runs. Origins of this odd black market can be traced to the confluence of three seemingly random elements:
* A crackdown on athlete defections by Cuban leader Fidel Castro’s government that has intensified over the last decade;
* Exceptions to federal immigration policy that apply uniquely to Cubans seeking asylum;
* Uncertain enforcement of arcane rules by Major League Baseball dating back 30 years that reflect baseball’s efforts to conform with the U.S. embargo on trade with Cuba.
Joe Kehoskie, a Syracuse, N.Y., sports agent who has represented more than a dozen Cuban athletes, said the smuggling of baseball players “has become a cottage industry,” an example, he said, of “bare-knuckles capitalism.”
A rash of defections by prominent ballplayers during the 1990s prompted Castro’s government to impose restrictions on Cuban players and teams engaged in international competition. Those restrictions became most severe after the 2002 defection of pitcher Jose Contreras, now with the Chicago White Sox.
Cuban authorities ordered widespread suspensions of players seen as defection risks. Since then, only one is known to have defected at an international event -- while smuggling has soared.
“It’s like somebody threw a switch,” Kehoskie said. “They stopped defecting at tournaments and they all started taking speedboats to Miami.”
The timing of changes to Washington’s policy added to favorable conditions for smuggling.
Since the mid-1990s, Cuban immigrants -- like others from Haiti or elsewhere -- have been turned back if intercepted at sea, but they are allowed to remain in this country legally simply by reaching shore anywhere in the U.S.
The unique rule for Cubans has led to some rough landings. One smuggling run in the summer of 2004 ended when the pilot ran his boat full-throttle onto a Florida beach, saving his passengers a return trip to Cuba.
Major League Baseball’s rules are more complicated, but equally arbitrary as they apply to Cubans.
Under terms of the 1970s-vintage Kuhn Initiative, named after then-Commissioner Bowie Kuhn, U.S. teams were barred from signing players living in Cuba to contracts -- an extension of State Department bans on American companies doing business with Cuba.
Arriving on the shores of Florida makes a Cuban defector eligible for U.S. residency, however, and subject to Major League Baseball’s annual amateur draft. The player then can negotiate only with the team that selected him in the draft.
To encourage more-lucrative bidding wars, agents generally advise Cuban players to seek residency outside the United States, allowing them to negotiate with multiple teams as free agents under baseball’s rules.
Contreras, for example, claimed Nicaraguan residency after his 2002 defection, then signed a $32-million contract with the New York Yankees.
Risks and rewards
It took two tries during the summer of 2004 for the five players in Medina’s boat to reach Florida.
A month earlier, the same players -- along with 17 other Cuban passengers -- were intercepted approaching the Keys. Customs agents fired on the speedboat, disabling its engine, then arrested the pilot and sent all the passengers back to Cuba.
One of them was Yoankis Turino, a left-handed pitcher who, by his own count, had been frustrated attempting to leave Cuba on 10 previous occasions.
He testified in a Key West court this year that the last offer of transit to Florida came in a phone call from someone named Javier, inviting him to rendezvous with the speedboat at night off a Matanzas beach on the north shore of Cuba.
“Javier said not to worry, that we would be able to make lots of money playing baseball,” Turino told the court.
The caller was really Medina, but Turino was ready to leave with Bozo the Clown had he offered to get him out of Cuba. The pitcher, dropped from his team as a potential defector, had missed two baseball seasons.
For the same reason, pitcher Francisely Bueno was bumped from the Cuban Olympic team that summer. He and Turino had been teammates on Havana’s powerful Industriales -- the Cuban version of the Yankees.
They joined other suspended defection risks -- Allen Guevara, Osmany Masso and Osbek Castillo -- boarding Medina’s boat in the darkness off Matanzas.
Potential risks and rewards were well-known. Despite severe news censorship in Cuba, Contreras’ $32-million contract was famous. So were “El Duque’s” $6.6-million signing bonus with the Yankees and Yuniesky Betancourt’s $2.8-million deal with the Seattle Mariners.
Finally, after reaching Big Pine Key the night of Aug. 22, 2004, it looked as though five more Cuban ballplayers were about to realize similar dreams.
First, however, they faced a three-day ride across the country to Southern California in a rented van.
In Los Angeles, the five newly arrived ballplayers were greeted at a Cuban restaurant in the San Fernando Valley by Gustavo “Gus” Dominguez, a former Cal State Northridge pitcher who was a professional baseball agent.
He had corporate apartments waiting for them in Woodland Hills. He arranged for them to work out daily with the Pierce College baseball team.
All five signed representation contracts with Dominguez, co-founder of Total Sports International. Court records would later show that the contracts were postdated, falsely indicating they were signed a month before the players even reached Florida.
Through Dominguez, the Cubans eventually auditioned for more than 30 scouts representing 23 major league teams. The players generated modest interest -- enough for some of them to take another big gamble.
In December, nearly four months after their night landing on Big Pine Key, three of the Cuban ballplayers flew by private plane to Santo Domingo in the Dominican Republic -- a move that risked erasing the path to U.S. residency gained by reaching Florida in the first place.
The three athletes each applied for Dominican residency, a process that took nearly eight months. Finally, as official Dominican residents, they were granted visas sponsored by major league baseball clubs and returned to the United States.
While these Cuban ballplayers, like many others, openly shopped for foreign residency, organized baseball took little notice. Such passive response not only has helped foster a black market in smuggled players, but it has contributed to baseball’s inconsistent rulings.
Take for example the cases of Angels slugger Kendry Morales and highly regarded Atlanta Braves player Yunel Escobar -- both smuggled from Cuba around the same time.
Morales landed an agent and obtained Dominican residency -- approved by the baseball commissioner’s office -- then negotiated a $10-million contract with a $3-million signing bonus. Escobar’s agent, however, made no effort to gain foreign residency for his client, who wound up relegated to the 2005 draft and signed for about $475,000.
Two players, same homeland, smuggled into the United States in the same year, end up with very different results. Morales has bounced between the Angels and the minor leagues. Escobar has been starting in the Braves’ infield.
“Baseball’s policy might have made sense initially, but over time it has morphed into a policy that punishes legal activity while rewarding illegal activity,” agent Kehoskie said.
Lou Melendez, vice president of international relations for baseball Commissioner Bud Selig, defended baseball’s policies and practices. He said verifying all claims would require enlisting teams of private investigators.
“You have to rely to a certain extent on the representations made to you by the player and by the agent that’s representing him,” Melendez said.
But as Selig’s point man on Cuban ballplayers, Melendez conceded that continuing controversies over ballplayer smuggling could “require us to take a good, hard look at the policy.”
Going after the agents
Medina the smuggler could end up playing a pivotal role in forcing such a reassessment.
Already his cooperation with law enforcement authorities has shaken the world of baseball agents. His testimony this year helped convict Dominguez of federal charges related to the Matanzas smuggling run.
The Encino agent’s case has been closely monitored by other agents and the Cuban exile community, where Dominguez is considered a heroic figure for helping Cuban ballplayers.
“They’re going to go after more agents,” warned Juan Iglesias, a Miami-based player representative who has worked with Cuban defectors as well. “It’s sad that they’re using [Dominguez] as a steppingstone to more things.”
Secrets of the smuggling operation that landed Dominguez in legal trouble began unraveling early in the 2005 baseball season when Medina was intercepted on his way to a White Sox game in Chicago.
Confronted with evidence of past drug smuggling and insurance fraud, Medina sought to avoid heavy prison time by telling federal agents what he knew about sneaking in Cuban baseball players.
The information led authorities to Dominguez, but others also were implicated. Medina testified, for example, that a Florida agent once paid him $35,000 as a down payment to smuggle six other players. That agent has not been indicted.
Success has been elusive for many ballplayers.
Guevara returned to South Florida without seeking foreign residency. He works in construction. Masso was selected by the Arizona Diamondbacks in the 2006 draft but never signed a contract. He went to work in a Florida supermarket.
The three Dominguez clients who obtained Dominican residency fared only somewhat better.
Despite his foreign residency, Castillo wound up in the amateur draft, where he was selected in the 33rd round. He was the 987th player chosen overall. Most recently, Castillo was pitching for a minor league team, the Mobile (Ala.) BayBears.
Bueno signed a modest free-agent contract with the Braves and promptly went on the disabled list. He finished that first season with a 1-7 record. This year he has pitched in the minor leagues for the Mississippi Braves.
Turino was released in January by the Lincoln (Neb.) Saltdogs of the American Assn. of Independent Professional Baseball.
He now works in a Los Angeles factory that makes electrical parts for helicopters.
Dominguez, meanwhile, faces a federal prison term of three to five years. His sentencing is scheduled for July 9 in Key West. It is unclear how or whether the prosecution of Dominguez might affect the way sports agents deal with future Cuban defectors.
In the meantime, smuggling boats keep crossing the Florida Straits.
"[Smuggling] people and baseball players -- that’s never going to be over as long as the bearded one is over there,” Miami agent Henry Vilar said of Castro.