Orioles and Cuba shake hands, circa 1999.
Orioles and Cubans shake hands, circa 1999.

American aid worker and Maryland resident Alan Gross was released from a Cuban prison after five years this morning. By noon, President Barack Obama announced a “new chapter” in relations with our Caribbean neighbor, which includes easing the ban on traveling to Cuba, and making moves to lift America’s longtime economic embargo against the Communist nation. The morning developments marked a swift turnaround after 50 years of hard-line stances toward Cuba that were filled with plenty of tense moments and high political theatre. In 1999, the Orioles were a part of the diplomatic dance.

After shuttle diplomacy back and forth to Havana by O’s owner Peter Angelos, the Orioles played the Cuba’s national team in a pair of exhibition games in 1999, one of which represented the first time an American team played in Havana since 1959. On the field, the teams split the series 1-1, with each taking an away victory.  The struggling O’s 12-6 loss at Camden Yards angered MLB players at the time, but the games didn’t end up on this Washington Post recap of Cuban-American relations because of the score. It was all about the politics.

The State Department and Fidel Castro were involved, but Angelos emerged as the episode’s chief political actor. Angelos pushed for three years to get the game before the Clinton administration finally relented. The real diplomats realized they needed cover to send a baseball team to a country the U.S. tried to invade.

Secretary of State Madeleine Albright told PBS’ Jim Lehrer that the purpose of sending the O’s was “to try to create some space for the Cuban people to be able to undertake some activity independent of the repressive state and to try to get some money to some of the families and people and entities, the private entities there.” All proceeds from the game benefitted the Caritas charity instead of the regime, and the administration also used the event to re-establish direct mail service with Cuba.

When the game arrived, the media sang Angelos’ praises as the true architect of the event. With U.S. leaders not making the trip for obvious reasons, it was Angelos and MLB Commissioner Bud Selig who sat with Fidel Castro.

Castro greets Peter Angelos (AP Photo/Roberto Borea)
Castro greets Peter Angelos (AP Photo/Roberto Borea)

“He felt that something could be achieved by the people getting together and playing a baseball game,” Angelos’ son Louis told the Los Angeles Times. “He said, ‘Why not just go and play? Nothing bad can come from it.”‘

Like Obama does today, Angelos had his critics. A Cuban democracy advocate told the Times that the move was “prolonging the suffering” of people who lived in Cuba.

After the series, the Orioles learned that diplomatic gestures toward Cuba are one thing, but making policy toward the country is another matter altogether. After Angelos made all of that effort to open baseball relations, then-Orioles general manager Syd Thrift said the team wouldn’t sign Cuban players who defected because Angelos didn’t want to “do anything that could be interpreted as being disrespectful or … encouraging players to defect.”

A federal investigation ultimately found the Orioles did nothing wrong, and Angelos later reversed the policy. Henry Urrutia debuted with the club in 2013 after defecting, and the Orioles are grooming Cubans Daniel Alvarez and recently-signed Elier Leyva in their farm system.

Angelos also hasn’t dropped the idea of returning to Cuba, last floating it in 2009. With the travel ban now relaxed, maybe Angelos can help organize another game. After all, the series is still tied at 1-1.

Stephen Babcock is the editor of Technical.ly Baltimore and an editor-at-large of Baltimore Fishbowl.