Breaking the Embargo

On This Day in 2008, the US's Historic Return to Cuban Soil Netted a Win in World Cup Qualifying

The comprehensive dismantling of Barbados had served its purpose—ending the Americans' goalless drought and launching them into the semifinals of CONCACAF World Cup qualifying. But as Bob Bradley's squad prepared for the next phase, they faced a challenge that transcended soccer: becoming the first U.S. men's team to play on Cuban soil in 61 years.

The semifinal round had drawn the United States into Group One alongside Cuba, Guatemala, and Trinidad & Tobago. Only the top two finishers would advance to the final hexagonal, where three automatic World Cup berths awaited. The Americans had opened strongly on August 20 with a workmanlike 1-0 victory over Guatemala, Landon Donovan converting a penalty kick in the second half to secure three crucial points on the road.

But Guatemala was merely the appetizer. The main course would be served at the crumbling Estadio Pedro Marrero in Havana, where politics and sport would collide in ways that dwarfed any tactical considerations. The last time American and Cuban flags had hung in the same stadium was February 14, 1947, when Cuba defeated the visiting Americans 5-2 in a friendly match. 61 years later, those same colors would meet again under vastly different circumstances. The 1962 economic embargo had transformed what should have been a routine qualifying match into a diplomatic minefield, complete with visa applications, restricted travel, and the ever-present specter of player defections.

The bureaucratic hurdles had been immense. Months of paperwork, coordination with the U.S. Olympic Committee, and careful navigation of travel restrictions had preceded the team's charter flight to Havana. As the Americans stepped off the plane on Thursday, they entered a world frozen in time. Danny Califf captured the surreal atmosphere perfectly: "It's like stepping out of a time machine. It's just surreal with the buildings and the cars." Havana's streets, populated by American automobiles from the 1950s and buildings lacking some paint, provided a stark backdrop to their World Cup ambitions.

The night of September 6 arrived with the sticky, oppressive heat that characterizes Caribbean evenings. The Estadio Pedro Marrero, showing its age like much of Havana, would host approximately 8,000 spectators—a modest crowd by soccer standards but electric with anticipation. Tickets had been priced at just one peso (roughly five American cents), and the government had bused in students and youth groups to create atmosphere for their amateur national team.

A thunderstorm had soaked the field two hours before kickoff, creating treacherous conditions that would favor neither team's technical approach. When the teams took the field, the political undertones were immediately apparent. Cuban fans booed the Americans during their warm-up but respectfully applauded during formal introductions—a complex reaction that reflected the island's relationship with their northern neighbors. The breakthrough came in the 39th minute through a sequence through a little chaos. Oguchi Onyewu, the towering center-back, launched a hopeful pass toward the Cuban penalty area from midfield. As the ball arced through the soggy air, Clint Dempsey rose with two Cuban defenders in a crowded aerial challenge.

In the confusion, one of the Cuban defenders inadvertently headed the ball directly to Brian Ching, who had positioned himself cleverly near the penalty spot. The MLS veteran held off his marker and calmly dropped the ball into the path of Dempsey, who found himself virtually unmarked 12 yards from goal. The Fulham midfielder made no mistake, slotting home what would prove to be the match's only goal.

"Ching somehow ended up getting himself in front of the defender and doing a good job of shaking him and giving me a good pass that allowed me to score," Dempsey reflected afterward. "Without him being there, I don't think I would have gotten that opportunity."

The goal seemed to deflate the Cuban crowd momentarily, but they quickly regrouped. The Americans, meanwhile, settled into a defensive posture that had become their calling card in qualifying—protecting leads through tactical discipline rather than expansive play. As the second half progressed, Cuba began to generate more dangerous moments. In the 56th minute, they created their clearest opportunity when Pedro Silvio found substitute Aliani Cervantes unmarked on the left side of the penalty area. Cervantes unleashed a powerful shot that forced Tim Howard into a diving save, with two Cuban players lurking nearby for a potential rebound.

Then, in the 86th minute, the match took a surreal turn. Half the floodlights at the aging stadium suddenly went out, plunging portions of the field into near-darkness. Play was briefly halted as officials assessed whether the match could continue safely. The delay seemed to energize the Cuban fans, who increased their vocal support during the unexpected intermission. When play resumed in the gloom, Cuba nearly found their equalizer. A free kick in the 88th minute created chaos in the American penalty area, with the ball ricocheting unpredictably before squirting toward goal. Howard had to make a desperate diving save to his left. "Crazy bounces happen like that," Howard said afterward. "If that goes in we're going home with our heads hung low."

When the final whistle finally sounded, the United States had secured a historic 1-0 victory—their first on Cuban soil since 1947. The margin was narrow, but the significance was immense. They had navigated not just the tactical challenge of beating a motivated opponent, but also the psychological pressure of playing in one of the world's most politically charged sporting environments.

"They did a pretty good job of making it hard on us," Donovan admitted. "They never really took the chances to get back in the game, so it kind of limited itself to trying to get the second goal if we could, but we felt that they weren't going to have real chances."

The victory moved the United States to six points from two matches in Group One, putting them in a prime position to advance to the final qualifying round. But there was no time for extended celebration—Trinidad & Tobago awaited four days later in Bridgeview, Illinois. Michael Bradley and Clint Dempsey scored first-half goals eight minutes apart, with Brian Ching adding a third early in the second half to complete a comprehensive 3-0 victory. With Tim Howard posting his third consecutive shutout, the Americans had opened the semifinal round with a perfect 3-0-0 record.

The Cuba match would be remembered not just for its political significance but also as the moment when Bradley's young team proved it could handle pressure in the most unlikely circumstances. They had broken a 61-year diplomatic silence with their feet, carrying American soccer into uncharted territory both literally and figuratively.