Remembering the Orioles' trip to Castro's Cuba in 1999

March 28, 1999 was one of the most significant days in baseball history, as it marked the first game for a major-league team in Cuba in 40 years.

The Orioles and Cuba's national team played the first of two exhibition games that day, in Havana; the second game was contested May 3, 1999, in Baltimore.

The O's won 3-2 in Game 1, but lost 12-6 in Game 2.

In 1959, Fidel Castro, who died Friday at age 90, led the Cuban Revolution to overthrow president Fulgencio Batista. His Communist regime put his country at odds with the United States, which placed a commercial, economic, and financial embargo on Cuba.

But with the aid of U.S. President Bill Clinton, who loosened some restrictions on Cuba, Orioles owner Peter Angelos was able to secure approval for the series.

“I always felt the embargo was a mistake and it did not work. In my mind, it was unfortunate and never should have happened," Angelos told The New York Times. "So I felt we had to put all that aside and re-establish the dialogue. I felt the two countries could get together and put behind their differences, and what better way to start than through baseball, the national sport of both countries?”

Many opposed the games, including MLB umpires and Cuban-American slugger Rafael Palmeiro, who refused to travel to the island nation. Ahead of the exhibitions, Cuba jailed four dissidents for speaking out against Castro's government, leading Cuban-American groups to call on the Orioles to cancel their plans.

Before the opener in Havana, Castro shook hands with the Orioles and the American anthem was played at Estadio Latinoamericano.

"He told me this was a good baseball town," then-Orioles manager Ray Miller said, according to The Associated Press. "He said not to worry, that we were playing in front of the greatest baseball fans in the world."

In the years leading up to the game, notable MLBers Livan Hernandez, Orlando Hernandez, and Rey Ordonez defected from Cuba for careers in the United States. Jose Contreras, who was on the mound for Cuba's upset victory over Baltimore, defected three years later.