‘The Kids We’re Helping Are Like Walking Lotto Tickets’

As far as athlete extractions from Cuba go, there’s no manual, no database and, often, no rules. Most athletes turn to smugglers, hiring coyotes often linked with cartels and organized crime syndicates. Some climb on dangerous speedboats.

The athletes assume these risks for a number of reasons. They might not know of an alternative way out. They might know someone who escaped Cuba without harm. Mostly, though, those methods represent the fastest way from their old life to their new one. Still, there are risks. In 2012 outfielder Yasiel Puig was threatened and held for ransom in Mexico by the Zetas cartel. In ’13, José Abreu, a first baseman for the White Sox, used a fake passport to board a flight from Haiti to Miami, but ate it en route because U.S. law, at the time, allowed Cubans arriving without travel documents to stay. Those who fail in fleeing—like Yordenis Ugás, the boxer who didn’t successfully defect until his sixth attempt—get thrown into detention centers.

Seven years ago, Jo started her foray into this secretive corner of the sports world with a different thesis. A Cuban immigrant who had arrived in the U.S. with her family when she was 4, the issue was personal to her. She believed that there had to be a better way for athletes to defect—and that she, a restaurateur from Tampa with no experience, would be the one to find it.

The strategy she devised involved lawyers, time, safety precautions and a mountain of paperwork. Her preferred method is assisting defections to countries with friendly laws for establishing residency, like Mexico or Ecuador. There, the athletes will wait for months on end, impatience and desperation growing daily, as she works to obtain visas for legal entry to the U.S.

But even her way isn’t free of dangers. It stems from the waiting, combined with the value of the players she protects. To absorb those risks she needed Billy, a former college football player turned military and police officer.

He solved her issues. But over time, in doing that, he created a major problem of his own.