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As feds probe MLB’s Latin American operations, a flashy scout and contested deal draw interest

Rudy Santín , former longtime scout for the Yankees, Rays and Giants, is one focus of an ongoing federal investigation of MLB operations in Latin America. (Will Hobson/The Washington Post)

SANTO DOMINGO, Dominican Republic — The diamonds in Rudy Santín ’s World Series ring sparkled in the light, along with gemstones that lined his gold bracelet and watch. Dressed casually except for leather Gucci loafers, the goateed, slightly rotund 59-year-old former major league scout ambled past a Mercedes-Benz in his driveway to greet two visitors one sweltering morning in May.

Santín ’s eye for big league talent has always made him money. For more than 30 years, that eye kept him employed as a scout for the New York Yankees, Tampa Bay Rays and San Francisco Giants. Even Santín ’s detractors — the ones who believe the allegations made by the Cuban player about Santín and threats made with machine guns — admit the man is a gifted scout.

Since going out on his own a few years ago as a buscón — the term for street agents who train young ballplayers here — Santín found Rafael Devers, the 22-year-old third baseman in the midst of a breakout season with the Boston Red Sox, as well as Wander Franco, the 18-year-old minor league shortstop for the Rays regarded as one of the game’s top prospects. But one of Santín ’s biggest busts has drawn the interest of federal law enforcement: Héctor Olivera, a once-prized Cuban infielder who fired Santín weeks before signing a $62.5 million contract with the Los Angeles Dodgers in 2015.

The circumstances surrounding Olivera’s path out of Cuba and eventual signing with the Dodgers are one focus of a wide-ranging Justice Department investigation of how Major League Baseball teams operate in Latin America, according to three people with knowledge of the probe who spoke on the condition of anonymity. The Justice Department declined to comment.

Olivera has testified to a federal grand jury in D.C., according to people with knowledge of the investigation, and two of Santín ’s former business associates also have been interviewed by federal agents.

Olivera declined to comment for this story through his lawyer, Miami attorney Frank Quintero Jr. But Dominican court documents from a legal battle between Olivera and Santín , obtained by The Washington Post, shed light on possible reasons for the federal authorities’ interest.

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Shortly after Olivera’s arrival in the Dominican Republic, court records show, he signed a “representation agreement” with a group of five people. One of them was Santín . None of them was a certified MLB agent.

Instead of charging Olivera 5 percent of his first professional contract — the typical maximum rate for an MLB agent — the contract called for Olivera to pay Santín ’s group 37.5 percent.

When told of the terms of this deal, Joe Kehoskie, a former agent and expert in the Latin American market, started laughing. It long has been an open secret among baseball scouts and agents that some elite Cuban players have been forced by smugglers to sign away exorbitant portions of their future earnings, as something of an exit toll off the island nation. According to Kehoskie, the contract between Olivera and Santín ’s group resembles one of these deals.

“There’s no legitimate reason for a player of Olivera’s caliber to have entered into an agreement like this, unless these were the people who brought him over, or they bought his rights from the people who brought him over,” Kehoskie said.

Quintero declined to discuss his client’s dealings with Santín in detail but did accuse Santín and his colleagues of threatening Olivera and his family members to try to coerce him into honoring their contract.

“These people were held against their will and supervised 24/7 by people carrying guns and were not allowed to freely move about the city unescorted,” Quintero said.

Over the course of a two-hour interview in May, Santín acknowledged his business partners probably financed Olivera’s smuggling out of Cuba, but he said he was not involved with those efforts. He expressed confusion about why federal authorities have interviewed two of his associates, and he said federal agents had yet to contact him directly. And he defended the 37.5-percent fee in the contract as a fair price for the training and financial support they provided.

Santín accused Olivera of inventing allegations made in their court battle: that Santín ’s business partners carried machine guns and that Olivera felt his safety depended on signing and honoring their contract.

“Fabricated bull----,” Santín said. Yes, one of his business partners carried a machine gun, Santín said, but it was to protect Olivera, not threaten him.

“Everybody owns a machine gun here, man,” Santín said. Besides, he added, his colleague who carried the machine gun was “like a teddy bear.”

Santín portrayed himself as the victim of a double cross involving the rival agent who eventually negotiated Olivera’s megadeal with the Dodgers: California-based Greg Genske .

According to Santín , just days before he and his associates were poised to strike a deal with the Dodgers, Genske secretly paid Olivera and one of Santín ’s business partners to permit Olivera to fire Santín and sign with Genske instead.

“He scammed everybody,” Santín said of Olivera.

Genske, whose roster of current and former clients includes Madison Bumgarner, CC Sabathia and Justin Turner, declined an interview request for this story. In response to an email outlining Santín ’s allegations, Genske called Santín “unreliable . . . with a long track record of deceit and dishonesty.”

“I did not bribe anyone ever,” Genske wrote. “Rudy’s hands are dirty in the Olivera matter. . . . He is properly the subject of governmental investigation.”

Roots go deep in Cuba

When word spread in the fall of 2014 that Olivera had fled Cuba and signed with Santín , it made sense, given Santín ’s deep connections in the Cuban baseball community.

Santín was born in Cuba in 1960 but lived there for just a few months before his family fled to Miami. As a youngster, he was a gifted pitcher with a rare talent: He was ambidextrous, and he threw from both sides of the mound. As a little leaguer, Santín developed a friendship with a fellow Cuban expatriate named Joe Cubas.

By the mid-1990s, Santín had advanced to director of Latin American scouting operations for the Yankees, and his old friend Cubas was “The Great Liberator,” according to “60 Minutes,” the agent who had enticed more than a dozen of Fidel Castro’s best ballplayers to defect, perhaps most famously pitcher Orlando “El Duque” Hernandez. Hollywood film producers considered turning Cubas’s life story into a movie.

But according to “The Duke of Havana,” a 2001 book about Hernandez’s defection, Santín claimed he was the real genius behind his old friend’s success.

“In the beginning, Santín was the mastermind, Cubas was his willing errand boy,” wrote authors Steve Fainaru and Ray Sanchez. In the book, Santín claimed he convinced Cubas to become an agent and target Cubans. Santín also said he suggested Cubas’s clients defect to countries other than the United States, so they could avoid the major league draft and be declared free agents, able to sign with the highest bidder.

“I was the one who thought up the whole idea,” Santín told Fainaru and Sanchez. “And anybody who tells you they had that figured out is lying.”

In a recent phone interview, Cubas said Santín was mistaken.

“Rudy is all about Rudy,” Cubas said. “He can take all the credit he wants, but I’ll let the facts and history tell the story.”

“The Duke of Havana” did not present Cubas and Santín , and their dealings with Cubans, in a positive light. In the book, a longtime former Yankees scout, Gordon Blakeley, accused the two of engaging in a bribe-kickback deal when Santín scouted for Tampa Bay.

According to Blakeley, Santín later bragged to him about the deal, in which Cubas agreed to steer pitcher Rolando Arrojo to sign with Tampa Bay in exchange for a bribe from the club, some of which Cubas kicked back to his “silent partner” Santín .

“It was $500,000 to Cubas and $50,000 to Rudy,” Blakeley said in the book. “Rudy’s a friend of mine. I guess he didn’t think it was that big of a deal.”

Reached by phone, Blakeley, now out of baseball, said the book quoted him accurately and declined further comment. Santín and Cubas repeatedly have denied the allegation, as has former Tampa Bay general manager Chuck LaMar.

Cubas said he left the agent industry in 2005, after the players’ union suspended his license amid accusations he had confiscated the immigration documents of a player who was trying to fire him, which Cubas denied. It was a good time to retire for someone who had made millions coaxing Cuban ballplayers to defect. The early 2000s saw a crackdown by federal law enforcement on illegal immigration, motivated in part by suspicions that violent Latin American drug cartels were moving into the business of smuggling elite Cuban ballplayers.

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In 2006, agent Gus Dominguez, one of Cubas’s major competitors for Cuban talent in the 1990s and 2000s, was indicted on several counts relating to accusations he financed the smuggling by boat of several Cubans into the United States. Dominguez was convicted of charges that included transporting and harboring aliens, and he served more than three years in prison.

Cubas had a falling-out with Santín a few years ago, he said, and they haven’t spoken since. He has monitored his old friend’s career from a distance with some concern, he said, as Santín left scouting and got involved in representing Cubans.

“In Rudy’s case,” Cubas said, “his mouth is usually what gets him in trouble.”

Recalling Olivera

The gated complex called Residencial Ebano hugs a main thoroughfare in Santo Domingo Este, a grittier part of the Dominican capital. Opposite the entrance is a string of casinos. At a nearby intersection, teenage boys converge upon idle cars, meager window washing tools at the ready, trying to earn a few pesos from willing customers.

Santín lives in a pale yellow cement condominium, with white columns and auburn trim, tucked in a corner of a side street.

After greeting two reporters one morning in May, Santín led them into a dimly lit room featuring a bar stocked with oversized bottles of top-shelf liquor, two flat-screen televisions connected to an expensive sound system, and a Jacuzzi.

Santín opened the interview by saying he shouldn’t discuss Olivera at all, given their legal dispute, and then proceeded to talk in detail about their dealings.

Olivera defected in September 2014, at the height of a big league gold rush on Cuban talent, fueled by the recent success of Yasiel Puig, José Abreu and Yoenis Céspedes. Olivera profiled as an impact second baseman with a good bat and a little bit of power. There were concerns about his age and his health, however. At 29, he was potentially past his prime, and a blood clot had limited his recent play.

In the days after Olivera’s defection, insiders speculated, if he passed a physical, he would easily receive a contract in the range of $30 million to $50 million over six years. If Olivera had entertained offers from multiple agents vying to represent him, the competition probably would have driven some agents to drop their fees to 4 percent. Instead, court records show, he signed with Santín ’s group within days of his arrival in the Dominican Republic, agreeing to pay 37.5 percent.

The Post was unable to locate the other four people named in the contract, one woman and three men, two of them brothers. Santín said that, before striking this agreement, he never knew any of his business partners on the Olivera deal and was vague about how they met. He said he received a phone call at some point in late 2014 from a man whose name he couldn’t recall, asking if he would be interested in working with Olivera. They sealed the deal at a nearby Applebee’s, Santín said, which is where he first met Olivera.

Santín said his job was to train Olivera and that the two brothers on the contract covered Olivera’s living expenses in Santo Domingo. As for the other two names on the contract, Santín said, he was unsure what they did. He speculated that, like other Cubans, Olivera fled the island by wading off the coast into a boat, which took him to the shores of Haiti, where law enforcement patrols are less frequent.

“At that time, that’s how most guys were coming over,” Santín said.

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Santín said he doubted his business partners directly oversaw the operation to smuggle Olivera, but that they most likely purchased Olivera’s rights from a man known for running these smuggling operations whom Santín could identify only as “some Haitian guy.”

Santín was unsure how much it costs to buy the rights to a Cuban star such as Olivera from smugglers but said he doubted it was an exorbitant sum.

“A dollar in Haiti goes a long way,” Santín said. “You would be surprised at the amount of money that things get done for, here and in Haiti.”

Santín had doubts about Olivera from the start, he said. Olivera would never look him in the eyes, Santín said, and he was often playing video games on his phone or looking off in the distance. Olivera regularly drank to excess, Santín said, and was so unreliable they needed to employ one person whose job was “awake guy,” meaning the person was responsible solely for waking up Olivera each morning.

Santín turned to another old friend to help get Olivera in shape: Angel “Nao” Presinal, a physical trainer with a colorful track record. In 2001, MLB banned Presinal from all league facilities after an incident in which airport authorities in Toronto accused the trainer and Juan Gonzalez, then one of Presinal’s top clients, of trying to bring through a bag containing anabolic steroids and hypodermic needles. (Presinal and Gonzalez accused each other of possessing the bag, and no criminal charges were filed.)

Interviewed outside his gym in Santo Domingo in May, Presinal said he regretted his decision to work with Santín and Olivera — because he was paid just $20,000 for several months of work, far less than he had expected. When asked how Olivera and other Cubans made it into the Dominican Republic, Presinal laughed.

“It’s a mystery,” he said in Spanish. When asked further questions about Olivera, Presinal briefly spoke three words in English — “My mind block” — and then made a gesture with his hand that seemed to simulate removing a piece of garbage from his brain, and throwing it away.

Bringing in an outsider

Because neither Santín nor any of his business partners on the contract with Olivera were registered MLB agents, they needed someone else to actually negotiate with the teams. For that, Santín brought in Manny Paula, a Miami-based agent and longtime business partner.

Paula declined to comment for this story through his attorney, Pittsburgh-based Jay Reisinger.

In the ensuing court battle between Olivera and Santín , however, Paula testified about his role. He said he intended to charge Olivera 4 percent for his services, which would have been paid in addition to the 37.5 percent Olivera already owed Santín and the four others. Paula testified he had no knowledge of the other contract Olivera signed with Santín ’s group.

“I do not know why there is a contract with Lazaro Santín and not me,” Paula said, using Santín ’s legal name.

In February 2015, negotiations between Paula and teams vying for Olivera began to heat up, Paula testified. The Atlanta Braves offered $50 million over six years; the Dodgers were considering going higher. Then, Santín got a phone call from Olivera, informing him he was firing all of them and signing with Genske.

A month later, Genske negotiated a six-year, $62.5 million contract for Olivera with the Dodgers, including a $28 million signing bonus. Had Santín been involved with that deal, per the terms of the contract he signed with Olivera, he would have made $2.5 million for about seven months of work.

Shortly after Olivera signed with the Dodgers, according to Santín , he got a phone call from a former colleague of Genske’s, who explained how Genske lured Olivera away: with money.

According to Santín , this colleague — whose name he could not recall — said Genske had paid an amount in the range of $200,000 to $500,000 to Olivera, which Olivera then split with one of Santín ’s associates to go along with the change in agents.

Over the next year, representatives of Olivera visited Santín and the others on the contract with checks for amounts ranging from $100,000 to $300,000. Before taking the checks, Santín and company needed to sign documents stating they relinquished the right to sue Olivera for breaking their contract.

Santín was the only one to refuse, and he sued Olivera, seeking his full payment.

“I said ‘You got to be crazy, bro,’ ” Santín said of his interaction with Olivera’s representative. “Take that check and stick it up his ass. That’s not 4 percent of what he got.”

Genske, while denying allegations he paid Olivera to sign with him, declined to elaborate on the situation.

“I’m in the process of writing a book that will include the true story re: Héctor’s representation,” Genske wrote in an email. “I appreciate your interest but I’d prefer to keep the true story fresh.”

In the past year, as word circulated through the Dominican baseball community of another American law enforcement investigation into the trafficking of Cuban players, two of Santín ’s associates have been contacted by federal agents: George Bautista, a batting coach who worked with Olivera, as well as Paula, the agent.

Paula, in turn, filed a grievance with the Major League Baseball Players Association against Genske. The MLBPA regulates agents, and paying a player to sign is a violation of the union’s rules for agents. The union declined to comment. According to three people with knowledge of the investigation, federal prosecutors in D.C. are also reviewing documents from this grievance as part of their investigation.

Just four months after the Dodgers signed Olivera, they traded him to the Braves as part of a three-team deal with the Miami Marlins. He played sparingly over parts of the next two seasons, then was suspended after an April 2016 arrest for assaulting a woman in Arlington, Va., during a series against the Washington Nationals. He was later convicted and traded to the San Diego Padres, who released him that August. He now lives in Miami, in a $1.9 million home he bought in 2015, months after he signed his deal with the Dodgers.

After sending subpoenas last year to clubs including the Dodgers, Braves and Padres, and getting Olivera’s testimony earlier this year in D.C., the Justice Department investigation has gone publicly quiet.

Santín , for his part, is unconcerned about the federal probe. He’s focused on his case in Dominican courts against Olivera, seeking the millions he believes he’s owed. According to Santín ’s lawyer, the case is set to be heard at some point over the next few months by the country’s Supreme Court.

Santín said his lawyer thinks he has a good case, but he expressed pessimism and concern that even his country’s highest court’s influence could be bought.

“I know how this town works,” Santín said. “It’s not a question of if it can be done. It’s how much can it be done for.”