When the Orioles traveled to Havana in 1999 to play a goodwill game against a team of Cuban All-Stars, it had been nearly 40 years since a major league team had set foot in the tiny island nation.
Little did anyone suspect at the time that it would be another 17 years before another big league team would do the same, but the Tampa Bay Rays will arrive in Cuba this week to play the Cuban national team against a much different geopolitical backdrop.
Relations between the United States and Cuba have eased to the point that President Barack Obama on Sunday will become the first sitting American president to walk on Cuban soil since Calvin Coolidge visited the country in 1928. Diplomatic relations have been restored, travel restrictions already have been loosened and there is growing sentiment that the stifling economic embargo imposed by the United States after Fidel Castro took power should be lifted.
The political landscape was much different when the Orioles first proposed their trip in the mid-1990s and were rebuffed by the U.S. State Department, but the Clinton administration eventually approved it as part of an initiative to expand contact with the Cuban people.
The game at Estadio Latinoamericano, followed five weeks later by another in Baltimore, was a moment in history that many thought at the time might signal a thaw in the tense relationship between the United States and Cuba.
Orioles owner Peter Angelos certainly hoped so, which is why he led a delegation to Havana in January of that year to make the two-game series — once a political impossibility — a politically sensitive reality.
"It was a truly satisfying experience," Angelos said Friday, "because these were people who were just like our people. They were people who loved baseball and there was nothing they wouldn't do for us while we were there."
That delegation included Angelos and his son Louis, club counsel H. Russell Smouse, representatives of both Major League Baseball and the players union, some Washington-based political consultants, a representative from Catholic Relief Services and one Baltimore Sun reporter who was not supposed to be part of the group.
Angelos included me in the traveling party — identified only as a "special advisor to the managing partner" — because he wanted to make sure there was someone there to chronicle what he expected to be a historic event.
The Cuban officials were neither fooled nor amused and Jose Villanueva Torre, Cuba's vice minister of sports, greeted me on the tarmac at Jose Marti International Airport by saying, "Welcome to Cuba, Peter Schmuck, special advisor to the managing partner of the Orioles from The Baltimore Sun."
Of course, there was never going to be any advising on my part. During the several days of negotiations, I traveled freely around Havana with Tom Garofalo of Catholic Relief Services (who speaks perfect Spanish) and only took part in the public events organized by the Cuban officials or the Orioles/MLB contingent. Angelos and then-MLB executive vice president Sandy Alderson briefed me after each day's meetings.
The act of scheduling two baseball games might seem simple enough, but the negotiations were very complicated. The two sides had to agree on a plan to distribute the proceeds of the event to charity, since that was a condition for state department approval. The Major League Baseball Players Association, represented by former player Tony Bernazard and active Orioles player B.J. Surhoff, had to sign off on the playing conditions, which was no small matter, and there were all sorts of logistical aspects to be worked out for each team to travel to the other's home country.
For example, just the act of MLB paying for outfield padding at the archaic Estadio Latinoamericano — which the union demanded for the safety of the Orioles players — required a state department exemption to overcome the trade embargo. It also required some touchy personal diplomacy on the part of Bernazard to convince the Cuban baseball officials that the stadium was not adequate without insulting them.
Meanwhile, predictable resistance was already building in the Cuban-American community, which would lead to demonstrations outside the Orioles' spring training home in Fort Lauderdale, Fla., before the team departed in late March.
But in January, the deal still wasn't done and the situation was complicated on both sides by suspicion over the Orioles' motives. The Cubans wondered if the Orioles had some ulterior reason for the goodwill trip, and for that matter, so did some of Angelos' fellow owners.
"[The Cubans] were leery," Angelos said, "and some of the other owners wanted to know what I was up to."
There was speculation that Angelos was trying to make a deal to funnel Cuban players to Baltimore, or at least make inroads in the Cuban baseball community in case the political situation changed enough to make those players available to major league clubs.
"That was being promulgated by some," Angelos said, "but I had no intention of going there for that purpose. I only wanted to go there because I felt the Cuban people were our friends and someone was always stoking animosity between our two peoples."
The most striking aspect of the first trip for me was how friendly the Cubans were toward visitors from a country that their government had been vilifying for four decades. Everywhere we went, we were approached on the street by regular people who asked us if we were Americans and then enthusiastically peppered us with questions.
Mostly, they wanted to know if the rumors were true that the Orioles — they pronounced the name "O-ree-O-lez" — were really coming to Cuba.
In one underground night club, one of the jazz musicians sat down at our table and asked where we were from. When I said I was originally from Los Angeles, he got very excited.
"Do you know Tom Waits?" he asked.
That night we got a lesson on the impact of the embargo. The band had trouble performing regularly because it was so difficult to find strings for their instruments. Garofalo, who traveled regularly to Cuba at the time, had him make a list of what he needed and vowed to bring him a supply on his next visit.
Our group also attended a Cuban National Series game, featuring the Havana Industriales and the team from Santiago de Cuba. We had heard about the unbridled enthusiasm of Cuban baseball fans and it was very much on display that day, though things almost got out of hand when some members of the delegation tried to distribute Orioles baseball caps to members of the crowd.
The trip for the actual game in Havana was more of a whirlwind. The Orioles, like the Rays this week, were in the middle of spring training and on a tight schedule, so there wasn't as much opportunity for interaction with the general public. Angelos, however, paid for a charter plane to bring 100 school-age kids to Havana to play ball with a similar group of Cuban children.
The game between the Orioles and a team of top Cuban players was controversial on several levels, starting with the fact that it was basically an invitation-only event controlled by the Cuban government.
Angelos and then-baseball commissioner Bud Selig would get some criticism at home for watching the internationally televised game alongside Castro. But Angelos made no apologies at the time, pointing out that the MLB contingent was a guest in Cuba and doing anything else would have been politically impolite.
Seventeen years later, Angelos now says that the highlight of both trips was witnessing the pregame flag ceremony that engaged the players and coaches from both teams.
"When Castro stood up and saluted our flag, that made the trip for me," Angelos said. "That made it all worthwhile."
Read more from columnist Peter Schmuck on his blog, "The Schmuck Stops Here," at baltimoresun.com/schmuckblog.