Rubio says current situation in Cuba is ‘unacceptable’
US Secretary of State Marco Rubio said on Tuesday (May 5) that the current situation in Cuba is unacceptable, adding that the US will address it, but not today.
Prediction market analysts are on the lookout for so-called “sharps”, insiders, and transactions they deem suspicious. One trader is keeping an eye on Cuba’s future.
An anonymous trader with the username JeffHK joined Polymarket in February and raised $57,500 in just one market: Will the US invade Cuba in 2026?
The “yes” bet on Cuba was so high in the young market that the odds actually moved against him, resulting in what experts call “slippage.”
“You either have someone who is very inexperienced or someone who is confident but unsophisticated,” says Gary Moreland, co-founder of Betting Intelligence. “This is such a high stakes that he may believe he knows something that others don’t.”
According to the company, the transaction had several questionable indicators. There were no preparatory trades, no diversification, no other portfolios. Just a few weeks after opening a new account, this huge position turned out to be well above the polymarket curve.
“The slippage that JeffHK endured on his largest trade represents either a clear error in his execution or a desperation to fill orders at any price point,” Dan Zimmerman, co-founder of Betting Intelligence, wrote in a report for USA TODAY.
The bet was made in the wake of a high-profile insider scandal involving military personnel charged with profiting from classified information in the U.S. raid on Venezuela.
Some lawmakers this week pledged to crack down on insider gambling.
Meanwhile, Polymarket says it has robust systems in place to detect insider trading. The company declined to comment on the specific Cuban market, but pointed to previous comments about the 38-year-old U.S. soldier who was indicted.
“We flagged this, referenced it, and collaborated throughout the process. Despite what many are led to believe, this happens all the time behind the scenes,” writes Polymarket founder and CEO Shayne Coplan. “The transparency afforded by on-chain markets makes global compliance more effective than ever. All transactions are public, permanent, and auditable. Bad actors leave traces.”
History of the Cuban market
Polymarket offers three markets related to Cuba, with various expressions ranging from “invasion” to “military conflict” to “military action”. Competitive Market Calci has a related market surrounding whether Cuban President Miguel Díaz-Canel will step down by the end of the year.
As of early May, the market was trending all the way down, with the probability of a spread occurring between about 21% and 45%.
After anonymous trader JeffHK made trades, astute countertraders intervened and drove down the value of his holdings, leaving him with a paper loss of $34,000 by the time USA TODAY began contacting investors in early May. Then, in the early morning hours of May 7th, JeffHK sold much of his “Yes” position, incurring a five-digit loss.
He remains the market’s top investor and could profit even if the U.S. invades by the end of the year.
The Cuban prediction market moved rapidly following the Trump administration news reported by USA TODAY. It happened in mid-March when the president announced “maximum pressure” on Havana, and then again in mid-April with news of a two-week deadline and talk of the release of prisoners by the United States.
Alex Goldenberg, founder of the intelligence firm Silent Index, said the widely publicized Justice Department charges against U.S. soldiers are likely to have a chilling effect on insiders. But he said the soldiers may have taken basic steps to hide their identities, which could have made them harder to detect.
And while millions of dollars are traded in the market by wealthy individuals looking for an edge, Goldenberg said Cuban intelligence and its allies in China and Russia are likely monitoring the market as well.
“It would be foolish not to pay attention to prediction markets,” Goldenberg said. “Because we’ve seen real-world sensitive information leaks that demonstrate real behavior.”
Other holders say they are confident
USA TODAY tracked down two other “Yes” holders who are convinced the U.S. will attack Cuba, including a Miami real estate agent and a “whale” who is a large and sophisticated trader.
The sixth highest “Yes” holder is Hugo Cardona Jr., who is called “Snowball Hustle” on the platform. Growing up in Miami, he says Cuba was always talked about. He said he was not an insider and said he had bet nearly $3,000 to take home $10,000 in the event of an invasion.
“Cuba is America’s ultimate real estate development project,” Cardona said. “Proximity is what makes all the difference, so I’m sure they’ll plan more proactively and aim for complete control.”
Cardona called Jeff Hong’s actions “very questionable,” but noted that prediction markets are full of gamblers and insiders willing to risk their careers for profit.
Nick Penzenstadler is a reporter with the USA TODAY investigative team. Contact us at npenz@usatoday.com or @npenzenstadler or call Signal (720) 507-5273.
